Name: 27914-60-9|4-(Allyloxy)benzoic acid|95%
Brand: Ambeed
SKU: A592968
Price: 55.0 USD
Availability: InStock
Rating: 90 (30 reviews)

1
[ 5443-37-8 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide In ethanol; water Heating;
	With potassium carbonate
	Stage #1: ethyl 4-(n-prop-2'-enyloxy)benzoate With potassium hydroxide In ethanol for 4h; Reflux; Stage #2: With hydrogenchloride In water

	With water; potassium hydroxide at 110℃; for 10h; Reflux;
	With potassium hydroxide In ethanol; water at 105℃; for 5h; Reflux;
	Stage #1: ethyl 4-(n-prop-2'-enyloxy)benzoate With water; sodium hydroxide In methanol for 3h; Reflux; Stage #2: With hydrogenchloride In water	The synthesis of 4-(5-hexenyloxy)benzoic acid (8) is described as follows: General procedure: Ethyl 4-(5-hexenyloxy)benzoate (1.2 g, 0.0048 mol) was added to a solution of sodium hydroxide (1.2 g, 0.030 mol) in 90 % methanol (30 mL). The solution was heated to reflux for 3 h. The solution was cooled and poured into 10 mL of 6 N HCl and the solution was then extracted with 30 mL of dichloromethane. The extraction solution was dried over anhydrous magnesium sulfate. Following removal of the solvent by evaporation under reduced pressure, the residue was purified by recrystallization from ethanol to yield 1.00 g (95 %) of white crystal.
	With potassium hydroxide at 105℃; for 5h;

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]
[2]Scichilone [Gazzetta Chimica Italiana, 1882, vol. 12, p. 452]
[3]Location in patent: experimental part Majumdar, Krishna C.; Chattopadhyay, Buddhadeb; Ansary, Inul [Canadian Journal of Chemistry, 2009, vol. 87, # 3, p. 472 - 477]
[4]Location in patent: experimental part Wu, Xiaojuan; Yu, Lilong; Cao, Hui; Guo, Renwei; Li, Kexuan; Cheng, Zihui; Wang, Feifei; Yang, Zhou; Yang, Huai [Polymer, 2011, vol. 52, # 25, p. 5836 - 5845]
[5]Yao, Wenhuan; Gao, Yanzi; Yuan, Xiao; He, Baofeng; Yu, Haifeng; Zhang, Lanying; Shen, Zhihao; He, Wanli; Yang, Zhou; Yang, Huai; Yang, Dengke [Journal of Materials Chemistry C, 2016, vol. 4, # 7, p. 1425 - 1440]
[6]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]
[7]Yao, Wenhuan; Gao, Yanzi; Li, Fasheng; Zhang, Lanying; Yang, Zhou; Yang, Huai [RSC Advances, 2016, vol. 6, # 90, p. 87502 - 87512] Yao, Wenhuan; Gao, Yanzi; Zhang, Cuihong; Li, Chenyue; Li, Fasheng; Yang, Zhou; Zhang, Lanying [Journal of Polymer Science, Part A: Polymer Chemistry, 2017, vol. 55, # 10, p. 1765 - 1772]

2
[ 27914-60-9 ]
[ 36844-51-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride at 20 - 55℃; for 7h;
91%	With oxalyl dichloride In dichloromethane at 20℃; for 3h;
90%	With thionyl chloride; N,N-dimethyl-formamide 1) room temperature, overnight, 2) 60 deg C, 2 h;

82%	With thionyl chloride at 20 - 60℃; for 7h;	4'-(4-(allyloxy) benzoyloxy) biphenyl-4-carboxylic acid (AOBA) 4-(allyloxy)benzoyl chloride (ABA-C) was prepared by 4-(allyloxy)benzoic acid (ABA was prepared according to ref. [33]) andthionyl chloride. A solution of ABA (20 g, 0.11 mol) and thionylchloride (35 mL) was placed into a round flask equipped with aabsorption apparatus to absorb hydrogen chloride. The mixturewas stirred at room temperature for 4 h, and heated to 60 C for 3 h.The excess thionyl chloride was distilled off under reduced pressure.ABA-C was obtained by distillation under reduced pressure.Yield: 82%.
79%	With thionyl chloride for 8h; Reflux; Inert atmosphere;
79%	With thionyl chloride
70%	With thionyl chloride at 65℃; for 6h;	1.2.2.2 (2.2) Preparation of intermediate 4-allyloxybenzoyl chloride: Add 49.72g (0.36mol) p-hydroxybenzoic acid in a 500mL three-necked flask,200mL of ethanol, 50mL of an aqueous solution of 40.40g (0.72mol) KOH and 1.66g (0.01mol) KI was added dropwise at room temperature. After cooling to room temperature, 43.55g (0.36mol) 3-bromopropene was added dropwise, and stirred at room temperature for 2h. Raise the temperature to 80, reflux for 15h,Cool to room temperature, pour the reaction solution into a beaker filled with a lot of water,Adjust the pH to 35 with dilute hydrochloric acid, filter and wash until neutral, and continue to wash the filter cake with hot water.Recrystallization from ethanol. Add 10.69g (0.06mol) to a 100mL round bottom flask4-allyloxy benzoic acid, 20mL thionyl chloride, heated to reflux at 65°C in an oil bath for 6h,After the completion of the reaction, it was distilled under reduced pressure to obtain 4-allyloxybenzoyl chloride, a light yellow transparent liquid, with a yield of 70%.
	With phosphorus trichloride
	With thionyl chloride
	With thionyl chloride; N,N-dimethyl-formamide Ambient temperature;
	With pyridine; thionyl chloride; N,N-dimethyl-formamide for 1h; Ambient temperature;
	With thionyl chloride In benzene for 2h; Heating;
	With thionyl chloride In N,N-dimethyl-formamide Heating;
	With thionyl chloride; N,N-dimethyl-formamide for 1h; Reflux;
	With thionyl chloride at 20℃; for 2h;
	With thionyl chloride In N,N-dimethyl-formamide
	With thionyl chloride at 90℃; for 6h;
	With thionyl chloride
	With thionyl chloride
	With thionyl chloride In N,N-dimethyl-formamide at 60℃; for 5h;	Synthesis of 4-AllyloxybenzoylChloride (Compound 2) The obtainedcompound 1 (14 g, 80 mmol) was reacted with thionyl chloride (12 mL, 165 mmol)containing a few drops of N,N-dimethylformamide (DMF) at 60C for 5 h. Then, 4-allyloxybenzoyl chloride (compound 2) was purified by reduced pressure distillation
	With thionyl chloride; N,N-dimethyl-formamide In toluene at 120℃; for 1h;	4.4. 4-Allyloxybenzoyl chloride 5a To a solution of 4-allyloxybenzoic acid (1.6 g, 9.0 mmol) in driedtoluene (18 mL) was added SOCl2 (3.6 mL, 45 mmol) and DMF(0.2 mL) under strong stirring. After stirred for 1 h at 120 C, thereaction mixture was concentrated under reduced pressure toafford crude 5a.
	With oxalyl dichloride In dichloromethane at 20℃; for 2h;	5 Step 5: Preparation of 4-(allyloxy)-N-(3-(benzy- loxy)phenethyl)-N-phenylbenzamide Step 5: Preparation of 4-(allyloxy)-N-(3-(benzyloxy)phenethyl)-N-phenylbenzamide To a solution of 4-allyloxybenzoic acid (4.58 g, 25.71 mmol, 1.30 eq) in dichloromethane (200 mL) was added oxalyl dichloride (5.02 g, 39.56 mmol, 3.46 mL, 2.00 eq). The resulting mixture was stirred at 20° C. for 2 hours. Then the mixture was concentrated to remove the solvent. The residue was dissolved in toluene (100 mL) and N-[2-(3-benzyloxyphenyl)ethyl]aniline (6 g, 19.78 mmol, 1.00 eq) and sodium carbonate (6.29 g, 59.34 mmol, 3.00 eq) was added. The resulting mixture was stirred at 100° C. for 2 hours. TLC (petroleum ether:ethyl acetate=3:1) indicated the reaction was complete. The reaction mixture was filtrated to remove the inorganic base, the filtrate was concentrated. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=30:1 to 10:1). The desired product 4-(allyloxy)-N-(3-(benzyloxy)phenethyl)-N-phenylbenzamide (8.00 g, yield: 87%) was obtained as a yellow oil. LC/MS (ESI) m/z: 464.1 [M+1]+; 1H-NMR (400 MHz, CDCl3) δ 7.46-7.34 (m, 5H), 7.28-7.15 (m, 6H), 6.92-6.83 (m, 5H), 6.71-6.67 (m, 2H), 6.04-5.97 (m, 1H), 5.41-5.35 (m, 1H), 5.28 (dq, J=10.4, 1.6 Hz, 1H), 5.05 (s, 2H), 4.48 (dt, J=5.2, 1.6 Hz, 2H), 4.15-4.10 (m, 2H), 3.03-2.99 (m, 2H).
	With thionyl chloride In benzene Reflux;	4.1.2 General procedure [74] for synthesis of substituted benzoyl chlorides General procedure: A mixture of the aromatic acid (2.500mmol), thionyl chloride (0.894g, 7.511mmol) and benzene (7mL) was refluxed for 3h. Then, benzene and the excess of thionyl chloride were distilled off. The crude acid chloride was weighed by difference and used directly in the next step without any further purification. For further purification, recrystallization from hexane may be performed. Crude yields of acyl chlorides 12a [75], 12b [76], 12c [77,78], 12d [79], 12e and 12f [80] were as high as 70-95%.
	With thionyl chloride	2.2.1. Synthesis of cholesteryl 4-(allyloxy) benzoate (MA) We synthesized monomer MA according to the previous method[21]. 4-(allyloxy) benzoic acid (IA) was synthesized by etherificationreaction between 3-bromo-prop-1-ene and 4-hydroxybenzoic acid.4-(allyloxy) benzoyl chloride (IB) was prepared by acyl chlorination ofIA. MA was obtained by esterification reaction between IB and cholesterol.
	With thionyl chloride at 70℃; for 5h;
	With thionyl chloride In toluene at 60℃; for 5h; Inert atmosphere;	1.2; 2.2; 3.2 2) Under a nitrogen atmosphere, place 1 mol of 4-allyloxy benzoic acid and 1 mol of thionyl chloride in a three-necked flask containing toluene, and react under reflux at 60° C. for 5 hours until the solution is clear. After the reaction, the excess toluene and thionyl chloride were distilled off under reduced pressure to obtain 4-allyloxybenzoyl chloride as a pale yellow liquid. Product ready for use;
	With thionyl chloride In toluene at 60℃; for 5h; Inert atmosphere;	1.2; 2.2 2) Under a nitrogen atmosphere, place 1 mol of 4-allyloxy benzoic acid and 1 mol of thionyl chloride in a three-necked flask containing toluene, and reflux for reaction at 60° C. for 5 hours until the solution is clear. After the reaction, the excess toluene and thionyl chloride were distilled off under reduced pressure to obtain 4-allyloxybenzoyl chloride as a pale yellow liquid. The product is ready for use.
	With sulfuryl dichloride Reflux;

Reference： [1]Han, Li; Ma, Hongwei; Li, Yang; Wu, Jian; Xu, Hanyan; Wang, Yurong [Macromolecules, 2015, vol. 48, # 4, p. 925 - 941]
[2]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]
[3]Apfel, M. A.; Finkelmann, H.; Janini, G. M.; Laub, R. J.; Luehmann, B.-H.; et al. [Analytical Chemistry, 1985, vol. 57, # 3, p. 651 - 658]
[4]Tian, Mei; Wu, Shuang-Jie; Tian, Xiao-Wei; Yao, Dan-Shu; Li, Chong-Liang; Hu, Jian-She; Zhang, Bao-Yan [Journal of Molecular Structure, 2016, vol. 1107, p. 202 - 213]
[5]Location in patent: experimental part Derdau, Volker; Fey, Thorsten; Atzrodt, Jens [Tetrahedron, 2010, vol. 66, # 7, p. 1472 - 1482]
[6]Atzrodt, Jens; Derdau, Volker; Holla, Wolfgang; Sandvoss, Martin [ARKIVOC, 2012, vol. 2012, # 3, p. 257 - 278]
[7]Current Patent Assignee: XUZHOU UNIVERSITY OF TECHNOLOGY - CN113201008, 2021, A Location in patent: Paragraph 0049; 0054; 0057-0058
[8]Pierce; Salsbury; Fredericksen [Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692]
[9]Kohjiya, S.; Ono, A.; Kishimoto, T.; Yamashita, S.; Yanase, H.; Asada, T. [Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 185, p. 183 - 197]
[10]Jones, Brian A.; Bradshaw, Jerald S.; Nishioka, Masaharu; Lee, Milton L. [Journal of Organic Chemistry, 1984, vol. 49, # 25, p. 4947 - 4951]
[11]Kossmehl, G.; Gerecke, B.; Harmsen, N.; Schroeder, F.; Vieth, H. M. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 269, p. 39 - 54]
[12]Zheng, Yiquan; Ren, Shaoping; Ling, Youdao; Lu, Mangeng [Molecular Crystals and Liquid Crystals, 2006, vol. 452, # 1, p. 3 - 9]
[13]Amigo, Maria; Terencio, Maria Carmen; Mitova, Maya; Iodice, Carmine; Paya, Miguel; De Rosa, Salvatore [Journal of Natural Products, 2004, vol. 67, # 9, p. 1459 - 1463]
[14]Location in patent: experimental part Majumdar, Krishna C.; Chattopadhyay, Buddhadeb; Ansary, Inul [Canadian Journal of Chemistry, 2009, vol. 87, # 3, p. 472 - 477]
[15]Location in patent: experimental part Brown, David P.; Wong, Thomas [Heterocycles, 2010, vol. 81, # 1, p. 149 - 161]
[16]Location in patent: scheme or table Xu, Xiao-Xu; Hong, Zhe; Liu, Fei [Molecular Crystals and Liquid Crystals, 2010, vol. 533, p. 52 - 62]
[17]Location in patent: experimental part Wu, Xiaojuan; Yu, Lilong; Cao, Hui; Guo, Renwei; Li, Kexuan; Cheng, Zihui; Wang, Feifei; Yang, Zhou; Yang, Huai [Polymer, 2011, vol. 52, # 25, p. 5836 - 5845]
[18]Location in patent: scheme or table Lee, Yi-Wen; Lin, Chih-Hung [Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5190 - 5194]
[19]Lee, Yi-Wen; Lin, Chih-Hung [Asian Journal of Chemistry, 2013, vol. 25, # 8, p. 4251 - 4255]
[20]Gao, Jianfeng; Sun, Zhongzhan; Peng, Tao; Yang, Lina [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 62 - 66]
[21]Yan, Shiqiang; Ren, Sumei; Ding, Ning; Li, Yingxia [Carbohydrate Research, 2018, vol. 460, p. 41 - 46]
[22]Current Patent Assignee: ARVINAS - US2018/155322, 2018, A1 Location in patent: Paragraph 1486; 1487
[23]AbdelHafez, El-Shimaa M. N.; Abdelhamid, Dalia; Aly, Omar M.; Maklad, Raed M. [Bioorganic Chemistry, 2020, vol. 99]
[24]Cong, Yue-hua; Gao, Shang; He, Xiao-zhi; Jia, Ying-gang; Liu, Ze-ping; Meng, Fan-bao; Zhang, Bao-yan [Dyes and Pigments, 2020, vol. 181]
[25]Daniliuc, Constantin G.; Gilmour, Ryan; Neufeld, Jessica; Sarie, Jérôme C.; Thiehoff, Christian [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 15069 - 15075][Angew. Chem., 2020, vol. 132, # 35, p. 15181 - 15187,7]
[26]Current Patent Assignee: GUANGDONG HINNO TECH - CN112679357, 2021, A Location in patent: Paragraph 0149; 0152; 0156; 0159; 0163; 0166
[27]Current Patent Assignee: GUANGDONG HINNO TECH - CN112694451, 2021, A Location in patent: Paragraph 0148-0153; 0155; 0160
[28]Fathalla, Walid; Pazdera, Pavel; Khalifa, Mohamed E.; Ali, Ibrahim A. I.; El Rayes, Samir M. [Journal of Heterocyclic Chemistry, 2022, vol. 59, # 5, p. 933 - 942]

3
[ 27914-60-9 ]
[ 1745-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With quinoline; copper at 200 - 210℃;

Reference： [1]Lauer; Leekley [Journal of the American Chemical Society, 1939, vol. 61, p. 3043,3046]

4
[ 27914-60-9 ]
[ 123-08-0 ]
[ 146028-57-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 4h; Ambient temperature;
95%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4.5h;
81.8%	Stage #1: 4-allyloxybenzoic acid; 4-hydroxy-benzaldehyde With dmap In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;	4.3.5 General procedure for the synthesis of aldehyde scaffolds 7a-7n and 8a-8n General procedure: 3-Hydroxybenzaldehyde (for 7a-7n) or 4-hydroxybenzaldehyde (for 8a-8n) (1.0g, 8.19mmol), DMAP (0.05g, 0.4mmol) and the corresponding 4-alkoxy benzoic acid (8.19mmol) were dissolved in DMF and stirred at room temperature for 15min. Then DCC (2.0g, 9.83mmol) was added drop wise to the reaction mixture. After completion of reaction, the reaction mixture was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water and brine solution. The organic portion was dried over sodium sulfate and concentrated under reduced pressure. The crude was then purified by column chromatography (silica gel 100-200 mesh) using ethyl acetate in hexanes to obtain the product.

Reference： [1]Kim, Hyun J.; Jackson, W. Roy [Tetrahedron Asymmetry, 1992, vol. 3, # 11, p. 1421 - 1430]
[2]Kim, Hyun J.; Jackson, W. Roy [Tetrahedron Asymmetry, 1994, vol. 5, # 8, p. 1541 - 1548]
[3]Datta, Dhrubajyoti; Debnath, Joy; Franzblau, Scott G.; Ghosh, Kalyan Sundar; Hari, Natarajan; Ma, Rui; Rana, Shiwani; Velappan, Anand Babu [Bioorganic Chemistry, 2020, vol. 103]

5
[ 106-95-6 ]
[ 99-96-7 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With n-Bu₄POH In tetrahydrofuran; water at 0 - 20℃;
91%	Stage #1: allyl bromide; 4-hydroxy-benzoic acid With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; Stage #2: With sodium hydroxide In 1,4-dioxane; water at 60℃; for 0.25h;
91%	With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 10h;	To a solution of 4-hydroxybenzoic acid (2.76 g, 20.0 mmol) in100mL DMF was added K2CO3 (11.04 g, 80.0 mmol), AllBr (5.3 mL,60.0 mmol) under strong stirring. After stirred for 10 h at 40 C, thereaction mixture was filtered and diluted with EtOAc (200 mL), andwashed with H2O (2 80 mL), saturated brine (2 80 mL). Theorganic layer was dried over Na2SO4, and concentrated underreduced pressure. Then the residue was dissolved in EtOH/H2O(100 mL, v: v 3:1), and KOH (2.24 g, 40.0 mmol) was added. Afterstirred for 1 h at 100 C, the solution was then evaporated to drynessand the colorless solid residue dissolved inwater (100 mL) andthe resulting stirred solution was acidified slowly with 50% H2SO4(6 mL). After stirring for ~30 min, the crystalline precipitate wasfiltered, washed with water and dried in vacuo to give 4-allyloxybenzoic acid as a white solid (3.22 g, 91%). 1H NMR(DMSO-d6, 400 MHz) d 7.88 (d, J 8.8 Hz, 2H), 7.02 (d, J 8.8 Hz,2H), 6.04 (ddd, J 22.4, 10.5, 5.2 Hz, 1H), 5.40 (dd, J 17.3, 1.4 Hz,1H), 5.27 (d, J 10.5 Hz, 1H), 4.63 (d, J 5.2 Hz, 2H); 13C NMR(DMSO-d6, 125 MHz) d 167.07, 161.84, 133.23, 131.40, 123.14, 117.91,114.54, 68.44.

90%	Stage #1: allyl bromide; 4-hydroxy-benzoic acid With potassium carbonate In N,N-dimethyl-formamide for 48h; Inert atmosphere; Stage #2: With water; sodium hydroxide In ethanol for 5h; Reflux; Inert atmosphere; Stage #3: With hydrogenchloride In ethanol; water Inert atmosphere;
90%	With potassium carbonate In N,N-dimethyl-formamide
90%	Stage #1: 4-hydroxy-benzoic acid With potassium iodide; potassium hydroxide In ethanol; water at 20℃; for 2h; Stage #2: allyl bromide In ethanol; water at 78℃; for 16h;
90%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	5 Example 5 Compound 1 (2.07g, 15mmol), allyl bromide (3.62g, 30mmol) and anhydrous potassium carbonate (10.2g, 73.9mmol) were dissolved in DMF (30mL) and stirred at room temperature for 48h. Then, 10 mL of water and 25 mL of dichloromethane were added to the reaction solution. After extracting the aqueous phase with dichloromethane three times, all the organic phases were dried with anhydrous sodium sulfate. Then, the solvent was evaporated under reduced pressure, and 50 mL of 2N NaOH and 10 mL of ethanol were added to the obtained residue. The mixed solution was heated to reflux and reacted for 5 hours. The pH of the reaction solution was adjusted to 1 with concentrated hydrochloric acid, and the precipitated solid was washed with ice water and ice methanol, and dried under vacuum to obtain compound 2 (2.4 g, yield 90%).
88%	Stage #1: allyl bromide; 4-hydroxy-benzoic acid With potassium carbonate In acetonitrile for 12h; Reflux; Stage #2: With water at 20℃; Alkaline conditions;
60%	With potassium hydroxide In methanol; water for 8h; Heating;
60%	With potassium hydroxide; sodium iodide In ethanol for 20h; Heating;
58%	Stage #1: allyl bromide; 4-hydroxy-benzoic acid With potassium iodide; potassium hydroxide In ethanol; water for 72h; Reflux; Stage #2: In water Acidic conditions;
33%	Stage #1: 4-hydroxy-benzoic acid With sodium iodide; potassium hydroxide In ethanol; water at 20℃; for 2h; Stage #2: allyl bromide In ethanol; water at 90℃; for 16h;	2 Step 2: Preparation of 4-allyloxybenzoic acid Step 2: Preparation of 4-allyloxybenzoic acid 4-Hydroxybenzoic acid (14 g, 101.36 mmol, 1.00 eq) was dissolved in ethanol (200 mL), then aqueous solution (50 mL) containing potassium hydroxide (14.22 g, 253.40 mmol, 2.50 eq) and sodium iodide (456 mg, 3.04 mmol, 0.03 eq) was added at 20° C. and the mixture was stirred at 20° C. for 2 hours. Then 3-bromoprop-1-ene (12.88 g, 106.43 mmol, 1.05 eq) was added dropwise. The resulting mixture was stirred at 90° C. for 16 hours. The desired product was detected by LC/MS. The reaction mixture was concentrated to remove the ethanol, the residue was neutralized with concentrated hydrochloric acid to pH around 3, and then extracted with ethyl acetate (300 mL*2), the combined organic phase was washed with brine (100 mL), dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=1:0 to 30:1). The desired product 4-allyloxybenzoic acid (6 g, 33.67 mmol, 33% yield) was obtained as a white solid. LC/MS (ESI) m/z: 179.0 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 12.65 (br, 1H), 7.89 (d, J=8.8 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 6.10-6.00 (m, 1H), 5.43 (d, J=17.2, 1.2 Hz, 1H), 5.28 (dd, J=10.4, 1.2 Hz, 1H), 4.64 (d, J=5.2 Hz, 2H).
31%	Stage #1: allyl bromide; 4-hydroxy-benzoic acid With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h; Stage #2: With sodium hydroxide at 20℃; for 18h; Stage #3: With hydrogenchloride
	With potassium hydroxide In methanol for 24h; Heating;
	With potassium hydroxide; potassium iodide
	With potassium hydroxide In methanol for 1h; Heating;
	With ethanol; water; potassium iodide; potassium hydroxide
	With potassium hydroxide In ethanol
	With potassium hydroxide In ethanol
	With potassium iodide; potassium hydroxide In ethanol
	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; Schlenk technique;
	With potassium iodide; potassium hydroxide	2.2.1. Synthesis of cholesteryl 4-(allyloxy) benzoate (MA) We synthesized monomer MA according to the previous method[21]. 4-(allyloxy) benzoic acid (IA) was synthesized by etherificationreaction between 3-bromo-prop-1-ene and 4-hydroxybenzoic acid.4-(allyloxy) benzoyl chloride (IB) was prepared by acyl chlorination ofIA. MA was obtained by esterification reaction between IB and cholesterol.
	With potassium iodide; potassium hydroxide In ethanol; water at 20 - 80℃; for 17h;	1.2.2.2 (2.2) Preparation of intermediate 4-allyloxybenzoyl chloride: Add 49.72g (0.36mol) p-hydroxybenzoic acid in a 500mL three-necked flask,200mL of ethanol, 50mL of an aqueous solution of 40.40g (0.72mol) KOH and 1.66g (0.01mol) KI was added dropwise at room temperature. After cooling to room temperature, 43.55g (0.36mol) 3-bromopropene was added dropwise, and stirred at room temperature for 2h. Raise the temperature to 80, reflux for 15h,Cool to room temperature, pour the reaction solution into a beaker filled with a lot of water,Adjust the pH to 35 with dilute hydrochloric acid, filter and wash until neutral, and continue to wash the filter cake with hot water.Recrystallization from ethanol. Add 10.69g (0.06mol) to a 100mL round bottom flask4-allyloxy benzoic acid, 20mL thionyl chloride, heated to reflux at 65°C in an oil bath for 6h,After the completion of the reaction, it was distilled under reduced pressure to obtain 4-allyloxybenzoyl chloride, a light yellow transparent liquid, with a yield of 70%.
	With potassium carbonate In acetone

Reference： [1]Liu, Pingli; Huang, Liang; Faul, Margaret M. [Tetrahedron Letters, 2007, vol. 48, # 41, p. 7380 - 7382]
[2]Harnoy, Assaf J.; Slor, Gadi; Tirosh, Einat; Amir, Roey J. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5813 - 5819]
[3]Yan, Shiqiang; Ren, Sumei; Ding, Ning; Li, Yingxia [Carbohydrate Research, 2018, vol. 460, p. 41 - 46]
[4]Location in patent: experimental part Derdau, Volker; Fey, Thorsten; Atzrodt, Jens [Tetrahedron, 2010, vol. 66, # 7, p. 1472 - 1482]
[5]Atzrodt, Jens; Derdau, Volker; Holla, Wolfgang; Sandvoss, Martin [ARKIVOC, 2012, vol. 2012, # 3, p. 257 - 278]
[6]Han, Li; Ma, Hongwei; Li, Yang; Wu, Jian; Xu, Hanyan; Wang, Yurong [Macromolecules, 2015, vol. 48, # 4, p. 925 - 941]
[7]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN111454288, 2020, A Location in patent: Paragraph 0133-0135
[8]Wen, Jiachen; Chennamadhavuni, Divya; Morel, Shana R.; Hadden, M. Kyle [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 9, p. 1290 - 1295]
[9]Apfel, M. A.; Finkelmann, H.; Janini, G. M.; Laub, R. J.; Luehmann, B.-H.; et al. [Analytical Chemistry, 1985, vol. 57, # 3, p. 651 - 658]
[10]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]
[11]Location in patent: experimental part Martinelli, Elisa; Paoli, Francesca; Gallot, Bernard; Galli, Giancarlo [Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 18, p. 4128 - 4139]
[12]Current Patent Assignee: ARVINAS - US2018/155322, 2018, A1 Location in patent: Paragraph 14780; 1481
[13]Location in patent: scheme or table Liu, Ligong; Li, Caiping; Cochran, Siska; Jimmink, Shane; Ferro, Vito [ChemMedChem, 2012, vol. 7, # 7, p. 1267 - 1275]
[14]Kohjiya, S.; Ono, A.; Kishimoto, T.; Yamashita, S.; Yanase, H.; Asada, T. [Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 185, p. 183 - 197]
[15]Hu, Jian-She; Zhang, Bao-Yan; Jia, Ying-Gang; Chen, Song [Macromolecules, 2003, vol. 36, # 24, p. 9060 - 9066]
[16]Amigo, Maria; Terencio, Maria Carmen; Mitova, Maya; Iodice, Carmine; Paya, Miguel; De Rosa, Salvatore [Journal of Natural Products, 2004, vol. 67, # 9, p. 1459 - 1463]
[17]Location in patent: scheme or table Xu, Xiao-Xu; Hong, Zhe; Liu, Fei [Molecular Crystals and Liquid Crystals, 2010, vol. 533, p. 52 - 62]
[18]Location in patent: scheme or table Lee, Yi-Wen; Lin, Chih-Hung [Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5190 - 5194]
[19]Lee, Yi-Wen; Lin, Chih-Hung [Asian Journal of Chemistry, 2013, vol. 25, # 8, p. 4251 - 4255]
[20]Gao, Jianfeng; Sun, Zhongzhan; Peng, Tao; Yang, Lina [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 62 - 66]
[21]Guo, Yuan-Qiang; Wang, Ruiguo; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Organic Letters, 2020, vol. 22, # 2, p. 709 - 713]
[22]Cong, Yue-hua; Gao, Shang; He, Xiao-zhi; Jia, Ying-gang; Liu, Ze-ping; Meng, Fan-bao; Zhang, Bao-yan [Dyes and Pigments, 2020, vol. 181]
[23]Current Patent Assignee: XUZHOU UNIVERSITY OF TECHNOLOGY - CN113201008, 2021, A Location in patent: Paragraph 0049; 0054; 0057-0058
[24]Fathalla, Walid; Pazdera, Pavel; Khalifa, Mohamed E.; Ali, Ibrahim A. I.; El Rayes, Samir M. [Journal of Heterocyclic Chemistry, 2022, vol. 59, # 5, p. 933 - 942]

6
[ 27914-60-9 ]
[ 99-96-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With cerium(III) chloride; sodium iodide In acetonitrile for 4h; Heating;
13 % Chromat.	With cerium(III) chloride; sodium iodide In acetonitrile for 20h; Heating;

Reference： [1]Thomas, R. Mathew; Reddy, G. Sudhakar; Iyengar [Tetrahedron Letters, 1999, vol. 40, # 40, p. 7293 - 7294]
[2]Bartoli; Cupone; Dalpozzo; De Nino; Maiuolo; Marcantoni; Procopio [Synlett, 2001, # 12, p. 1897 - 1900]

7
[ 40663-68-1 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 2-methyl-but-2-ene; polymer-supported chlorite; acetic acid In <i>tert</i>-butyl alcohol at 25℃;
93%	With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; for 12h; Sealed tube;
90%	With 4H₃N4H⁽¹⁺⁾CuMo₆O₁₈(OH)6^(4-); water; oxygen; sodium carbonate at 50℃; for 12h;

Reference： [1]Takemoto; Yasuda; Ley [Synlett, 2001, # 10, p. 1555 - 1556]
[2]Liu, Mingxin; Li, Chao-Jun [Angewandte Chemie - International Edition, 2016, vol. 55, # 36, p. 10806 - 10810][Angew. Chem., 2016, vol. 128, p. 10964 - 10968]
[3]Yu, Han; Ru, Shi; Zhai, Yongyan; Dai, Guoyong; Han, Sheng; Wei, Yongge [ChemCatChem, 2018, vol. 10, # 6, p. 1253 - 1257]

8
[ 106-95-6 ]
[ 176700-52-0 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydride In N,N-dimethyl-formamide at 20℃;

Reference： [1]Serrano-Wu, Michael H; Regueiro-Ren, Alicia; St. Laurent, Denis R; Carroll, Tina M; Balasubramanian, Balu N [Tetrahedron Letters, 2001, vol. 42, # 49, p. 8593 - 8595]

9
4-allyloxy-benzoic acid 3-methyl-but-2-enyl ester [ No CAS ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 4h;
87%	With cerium(III) chloride; sodium iodide In acetonitrile for 2h; Heating;

Reference： [1]Ramesh; Mahender; Ravindranath; Das, Biswanath [Tetrahedron Letters, 2003, vol. 44, # 7, p. 1465 - 1467]
[2]Yadav; Subba Reddy; Venkateshwara Rao; Chand; Prasad [Synlett, 2002, # 1, p. 137 - 139]

10
[ 95-71-6 ]
[ 27914-60-9 ]
[ 110204-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 25℃;

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

11
[ 26595-60-8 ]
[ 27914-60-9 ]
[ 99-96-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 92% 2: 8%	With aniline In toluene at 30℃; for 0.5h;

Reference： [1]Murakami, Hiromi; Minami, Tatsuya; Ozawa, Fumiyuki [Journal of Organic Chemistry, 2004, vol. 69, # 13, p. 4482 - 4486]

12
[ 27914-60-9 ]
[ 106-95-6 ]
[ 26595-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Murakami, Hiromi; Minami, Tatsuya; Ozawa, Fumiyuki [Journal of Organic Chemistry, 2004, vol. 69, # 13, p. 4482 - 4486]

13
[ 27914-60-9 ]
[ 5438-19-7 ]
[ 99-96-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 82% 2: 3%	With potassium hydroxide In methanol at 20℃; for 10h;

Reference： [1]Ishizaki, Miyuki; Yamada, Makoto; Watanabe, Shin-Ichi; Hoshino, Osamu; Nishitani, Kiyoshi; Hayashida, Maiko; Tanaka, Atsuko; Hara, Hiroshi [Tetrahedron, 2004, vol. 60, # 36, p. 7973 - 7981]

14
[ 27914-60-9 ]
[ 123-31-9 ]
[ 128422-75-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran

Reference： [1]Hu, Jian-She; Zhang, Bao-Yan; Jia, Ying-Gang; Chen, Song [Macromolecules, 2003, vol. 36, # 24, p. 9060 - 9066]

15
[ 3256-45-9 ]
[ 40663-68-1 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 49% 2: 35%	With 2.9-dimethyl-1,10-phenanthroline; oxygen; sodium hydrogencarbonate In water at 100℃; for 24h;

Reference： [1]Li, Huanrong; Guan, Bingtao; Wang, Wenjin; Xing, Dong; Fang, Zhao; Wan, Xiaobing; Yang, Liping; Shi, Zhangjie [Tetrahedron, 2007, vol. 63, # 35, p. 8430 - 8434]

16
[ 107-05-1 ]
[ 99-96-7 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With n-Bu₄POH In tetrahydrofuran; water at 0 - 20℃;

Reference： [1]Liu, Pingli; Huang, Liang; Faul, Margaret M. [Tetrahedron Letters, 2007, vol. 48, # 41, p. 7380 - 7382]

17
[ 35750-24-4 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
85.4%	With sodium hydroxide In 1,4-dioxane; water Reflux;	4.3 General procedure for 4-alkoxy benzoic acids (6a-6d) General procedure: 4-alkenyloxy methyl benzoate (28.0mmol) was dissolved in 1, 4-dioxane in water (1:1) followed by the addition of sodium hydroxide (84.0mmol) and maintained under reflux for 24-30h. After completion of reaction, volatiles were evaporated and the aqueous mass neutralized with concentrated hydrochloric acid. The white solid thus formed was filtered, washed thoroughly with water and dried to afford the benzoic acids. 4.3.1 4-(allyloxy)benzoic acid (6a) Yield- 85.4%; white solid; m.p- 142-144°C; 1H NMR (400MHz, CDCl3): δ 4.64 (d, J=5.4Hz, 2H), 5.34-5.37 (m, 1H), 5.46-5.48 (m, 1H), 6.05-6.11 (m, 1H), 6.99 (d, J=6.8Hz, 2ArH), 8.09 (d, J=6.8Hz, 2ArH). HRMS (ESI+): m/z calculated for C10H10O3 [M+H]+: 178.0630; found: 178.0633.
80%	With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
51%	With sodium hydroxide In methanol; water for 1.5h; Reflux;

50%	With sodium hydroxide In tetrahydrofuran; methanol; ethyl acetate	10 Example 10 Example 10 To a mixture of methyl 4-allyloxybenzoate (10.0 g), THF (50 mL) and methanol (50 mL) was added 2N aqueous NaOH solution (50 mL), and the mixture was stirred at 50° C. for 40 minutes. The reaction solution was concentrated to about 50 g, washed with hexane, and acidified with conc. hydrochloric acid. The precipitated crystals were collected by filtration, dissolved in ethyl acetate, dried over magnesium sulfate, and the solvent was evaproated under reduced prssure to give crude crystals of 4-allyloxybenzoic acid (4.68 g, 50%).
50%	With sodium hydroxide In tetrahydrofuran; methanol; ethyl acetate	10.1 (10-1) (10-1) To a mixture of methyl 4-allyloxybenzoate (10.0 g), THF (50 mL) and methanol (50 mL) was added 2N aqueous NaOH solution (50 mL), and the mixture was stirred at 50°C for 40 minutes. The reaction solution was concentrated to about 50 g, washed with hexane, and acidified with conc. hydrochloric acid. The precipitated crystals were collected by filtration, dissolved in ethyl acetate, dried over magnesium sulfate, and the solvent was evaproated under reduced prssure to give crude crystals of 4-allyloxybenzoic acid (4.68 g, 50 %).
	With sodium hydroxide In methanol

Reference： [1]Datta, Dhrubajyoti; Debnath, Joy; Franzblau, Scott G.; Ghosh, Kalyan Sundar; Hari, Natarajan; Ma, Rui; Rana, Shiwani; Velappan, Anand Babu [Bioorganic Chemistry, 2020, vol. 103]
[2]Cui, Yingjun; Zhang, Mengyi; Xu, Honglei; Zhang, Tingrong; Zhang, Songming; Zhao, Xiuhe; Jiang, Peng; Li, Jing; Ye, Baijun; Sun, Yuanjun; Wang, Mukuo; Deng, Yangping; Meng, Qing; Liu, Yang; Fu, Qiang; Lin, Jianping; Wang, Liang; Chen, Yue [Journal of Medicinal Chemistry, 2022, vol. 65, # 4, p. 2971 - 2987]
[3]Katsuki, Kaito; Kaneko, Kosuke; Kaneko, Kimiyoshi; Kato, Riki; Miyamoto, Nobuyoshi; Hanasaki, Tomonori [Journal of Organometallic Chemistry, 2019, vol. 886, p. 34 - 39]
[4]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); Sumitomo Pharma (in: Sumitomo Chemical); SUMITOMO CHEMICAL COMPANY LIMITED - US2003/181496, 2003, A1
[5]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); Sumitomo Pharma (in: Sumitomo Chemical); SUMITOMO CHEMICAL COMPANY LIMITED - EP1479384, 2004, A1
[6]Kaneko, Kosuke; Miwa, Yusuke; Nakamura, Naotake [Molecular Crystals and Liquid Crystals, 2007, vol. 473, # 1, p. 43 - 55]

18
[ 371-41-5 ]
[ 27914-60-9 ]
4-fluorophenyl 4-allyloxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With polyphosphate ester In diethyl ether for 24h; Heating;

Reference： [1]Kaneko, Kosuke; Miwa, Yusuke; Nakamura, Naotake [Molecular Crystals and Liquid Crystals, 2007, vol. 473, # 1, p. 43 - 55]

19
[ 27914-60-9 ]
di-p-allyloxybenzoyl avarol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / dimethylformamide / Heating 2: 100 percent / pyridine / 1 h / Heating

Reference： [1]Amigo, Maria; Terencio, Maria Carmen; Mitova, Maya; Iodice, Carmine; Paya, Miguel; De Rosa, Salvatore [Journal of Natural Products, 2004, vol. 67, # 9, p. 1459 - 1463]

20
[ 27914-60-9 ]
C₃₂H₃₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / tetrahydrofuran 2: 47 percent / Et₃N / CHCl₃ / 14 h / 20 °C

Reference： [1]Hu, Jian-She; Zhang, Bao-Yan; Jia, Ying-Gang; Chen, Song [Macromolecules, 2003, vol. 36, # 24, p. 9060 - 9066]

21
[ 27914-60-9 ]
[ 99-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃ / dimethylformamide / 20 °C 2: 96 percent / aniline / Pd(PPh₃)4 / tetrahydrofuran / 0.5 h / 20 °C

Reference： [1]Murakami, Hiromi; Minami, Tatsuya; Ozawa, Fumiyuki [Journal of Organic Chemistry, 2004, vol. 69, # 13, p. 4482 - 4486]

22
[ 120-47-8 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 81 percent / K₂CO₃ / ethanol / Heating 2: 82 percent / NaOH / H₂O; ethanol / Heating
	Multi-step reaction with 2 steps 1: alcoholic KOH-solution / 120 - 130 °C / Destillation des Reaktionsprodukts 2: aqueous potash
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 10 h / 85 °C / Reflux 2: potassium hydroxide / ethanol; water / 5 h / 105 °C / Reflux

	Multi-step reaction with 2 steps 1: potassium carbonate / butanone / 48 h / Reflux 2: sodium hydroxide; water / methanol / 3 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 10 h / 85 °C 2: potassium hydroxide / 5 h / 105 °C
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 10 h / 85 °C 2: potassium hydroxide / 5 h / 105 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]
[2]Scichilone [Gazzetta Chimica Italiana, 1882, vol. 12, p. 452]
[3]Yao, Wenhuan; Gao, Yanzi; Yuan, Xiao; He, Baofeng; Yu, Haifeng; Zhang, Lanying; Shen, Zhihao; He, Wanli; Yang, Zhou; Yang, Huai; Yang, Dengke [Journal of Materials Chemistry C, 2016, vol. 4, # 7, p. 1425 - 1440]
[4]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]
[5]Yao, Wenhuan; Gao, Yanzi; Li, Fasheng; Zhang, Lanying; Yang, Zhou; Yang, Huai [RSC Advances, 2016, vol. 6, # 90, p. 87502 - 87512]
[6]Yao, Wenhuan; Gao, Yanzi; Zhang, Cuihong; Li, Chenyue; Li, Fasheng; Yang, Zhou; Zhang, Lanying [Journal of Polymer Science, Part A: Polymer Chemistry, 2017, vol. 55, # 10, p. 1765 - 1772]

23
[ 27914-60-9 ]
[ 260403-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 46 percent / 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

24
[ 27914-60-9 ]
[ 408493-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 46 percent / 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

25
[ 27914-60-9 ]
C₃₃H₂₄Br₂F₁₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 46 percent / 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

26
[ 27914-60-9 ]
[ 260403-15-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

27
[ 27914-60-9 ]
[ 408493-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

28
[ 27914-60-9 ]
C₃₅H₂₄Br₂F₁₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

29
[ 27914-60-9 ]
endo-5-[[2',5'-bis[(4''-(n-(perfluoropropyl)propoxy)benzoyl)oxy]benzyl]oxy]carbonyl}bicyclo[2.2.1]hept-2-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 46 percent / 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating 4.1: dimethylsulfoxide; tetrahydrofuran / 22 h / 60 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

30
[ 27914-60-9 ]
exo-5-[[2',5'-bis[(4''-(n-(perfluoropropyl)propoxy)benzoyl)oxy]benzyl]oxy]carbonyl}bicyclo[2.2.1]hept-2-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 46 percent / 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating 4.1: dimethylsulfoxide; tetrahydrofuran / 22 h / 60 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

31
[ 27914-60-9 ]
endo-5-[[2',5'-bis[(4''-(n-(perfluorobutyl)propoxy)benzoyl)oxy]benzyl]oxy]carbonyl}bicyclo[2.2.1]hept-2-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating 4.1: dimethylsulfoxide; tetrahydrofuran / 22 h / 60 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

32
[ 27914-60-9 ]
exo-5-[[2',5'-bis[(4''-(n-(perfluorobutyl)propoxy)benzoyl)oxy]benzyl]oxy]carbonyl}bicyclo[2.2.1]hept-2-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: DCC; DMAP; p-TsOH / CH₂Cl₂ / 25 °C 2.1: 2,2'-azobisisobutyronitrile / toluene / 70 °C 2.2: 2,2'-azobisisobutyronitrile; tributyltin hydride / toluene / 2 h / 70 °C 3.1: 2,2'-azobisisobutyronitrile; N-bromosuccinimide / benzene / 4 h / Heating 4.1: dimethylsulfoxide; tetrahydrofuran / 22 h / 60 °C

Reference： [1]Small, Aaron C.; Pugh, Coleen [Macromolecules, 2002, vol. 35, # 6, p. 2105 - 2115]

33
[ 27914-60-9 ]
[ 645388-29-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: NaBH₄ / methanol / 1 h / 20 °C 5.1: 88 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C
	Multi-step reaction with 4 steps 1.1: oxalyl dichloride / dichloromethane / 2 h / 20 °C 2.1: sodium carbonate / toluene / 2 h / 100 °C 3.1: trichlorophosphate / toluene / 16 h / 120 °C 3.2: 2 h / 20 °C 4.1: triphenylphosphine; morpholine; palladium diacetate / tetrahydrofuran / 16 h / 20 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]
[2]Current Patent Assignee: ARVINAS - US2018/155322, 2018, A1

34
[ 27914-60-9 ]
[ 645388-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: diethyl ether / 18 h / Heating 5.1: 51 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

35
[ 27914-60-9 ]
[ 645387-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2: 83 percent / Na₂CO₃ / benzene / 2 h / Heating
	Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 2 h / 20 °C 2: sodium carbonate / toluene / 2 h / 100 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]
[2]Current Patent Assignee: ARVINAS - US2018/155322, 2018, A1

36
[ 27914-60-9 ]
[ 645388-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: NaBH₄ / methanol / 1 h / 20 °C
	Multi-step reaction with 3 steps 1.1: oxalyl dichloride / dichloromethane / 2 h / 20 °C 2.1: sodium carbonate / toluene / 2 h / 100 °C 3.1: trichlorophosphate / toluene / 16 h / 120 °C 3.2: 2 h / 20 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]
[2]Current Patent Assignee: ARVINAS - US2018/155322, 2018, A1

37
[ 27914-60-9 ]
[ 645388-28-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: diethyl ether / 18 h / Heating

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

38
[ 27914-60-9 ]
1-(4'-Pyrrolidinoethoxyphenyl)-2-phenyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: NaBH₄ / methanol / 1 h / 20 °C 5.1: 88 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C 7.1: conc. aq. HCl / 1 h / 90 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

39
[ 27914-60-9 ]
2-phenyl-1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-1,2,3,4-tetrahydroisoquinolin-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: NaBH₄ / methanol / 1 h / 20 °C 5.1: 88 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C 7.1: conc. aq. HCl / 1 h / 90 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

40
[ 27914-60-9 ]
1-methyl-2-phenyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1,2,3,4-tetrahydro-isoquinolin-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: diethyl ether / 18 h / Heating 5.1: 51 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C 7.1: conc. aq. HCl / 1 h / 90 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

41
[ 27914-60-9 ]
1-methyl-2-phenyl-1-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-1,2,3,4-tetrahydro-isoquinolin-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: diethyl ether / 18 h / Heating 5.1: 51 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C 7.1: conc. aq. HCl / 1 h / 90 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

42
[ 27914-60-9 ]
[ 645399-42-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: NaBH₄ / methanol / 1 h / 20 °C 5.1: 88 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

43
[ 27914-60-9 ]
[ 645399-58-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: diethyl ether / 18 h / Heating 5.1: 51 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

44
[ 27914-60-9 ]
[ 645399-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: NaBH₄ / methanol / 1 h / 20 °C 5.1: 88 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

45
[ 27914-60-9 ]
[ 645399-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI 4.1: diethyl ether / 18 h / Heating 5.1: 51 percent / Ph₃P; morpholine; Pd(OAc)2 / tetrahydrofuran / 18 h / 20 °C 6.1: NaH / dioxane / 80 °C

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

46
[ 27914-60-9 ]
1-(4-allyloxy-phenyl)-6-benzyloxy-2-phenyl-3,4-dihydro-isoquinolinium; iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 91 percent / (COCl)2 / CH₂Cl₂ / 3 h / 20 °C 2.1: 83 percent / Na₂CO₃ / benzene / 2 h / Heating 3.1: POCl₃ / 1.5 h / Heating 3.2: KI

Reference： [1]Renaud, Johanne; Bischoff, Serge François; Buhl, Thomas; Floersheim, Philipp; Fournier, Brigitte; Halleux, Christine; Kallen, Joerg; Keller, Hansjoerg; Schlaeppi, Jean-Marc; Stark, Wilhelm [Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2945 - 2957]

47
[ 27914-60-9 ]
[ 73376-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / SOCl₂, DMF / 1) room temperature, overnight, 2) 60 deg C, 2 h 2: 64 percent / pyridine / tetrahydrofuran / 1) room temperature, 4 h, 2) 60 deg C, 2 h

Reference： [1]Apfel, M. A.; Finkelmann, H.; Janini, G. M.; Laub, R. J.; Luehmann, B.-H.; et al. [Analytical Chemistry, 1985, vol. 57, # 3, p. 651 - 658]

48
[ 27914-60-9 ]
[ 83953-72-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / SOCl₂, DMF / 1) room temperature, overnight, 2) 60 deg C, 2 h 2: 75 percent / pyridine / 1) room temperature, 3 h, 2) 60 deg C, 2 h
	Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / dichloromethane
	Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / dichloromethane

Multi-step reaction with 2 steps 1: thionyl chloride / 6 h / 65 °C 2: pyridine / tetrahydrofuran / 10 h / Reflux

Reference： [1]Apfel, M. A.; Finkelmann, H.; Janini, G. M.; Laub, R. J.; Luehmann, B.-H.; et al. [Analytical Chemistry, 1985, vol. 57, # 3, p. 651 - 658]
[2]Lee, Yi-Wen; Lin, Chih-Hung [Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5190 - 5194]
[3]Lee, Yi-Wen; Lin, Chih-Hung [Asian Journal of Chemistry, 2013, vol. 25, # 8, p. 4251 - 4255]
[4]Current Patent Assignee: XUZHOU UNIVERSITY OF TECHNOLOGY - CN113201008, 2021, A

49
[ 27914-60-9 ]
[ 93001-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂, DMF / Ambient temperature 2: NEt₃ / CH₂Cl₂ / 2 h

Reference： [1]Jones, Brian A.; Bradshaw, Jerald S.; Nishioka, Masaharu; Lee, Milton L. [Journal of Organic Chemistry, 1984, vol. 49, # 25, p. 4947 - 4951]

50
[ 27914-60-9 ]
[ 73720-63-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper-powder; quinoline / 200 - 210 °C 2: pyridine

Reference： [1]Lauer; Leekley [Journal of the American Chemical Society, 1939, vol. 61, p. 3043,3046]

51
[ 26595-60-8 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,2'-azobis(isobutyronitrile) In benzene at 65 - 70℃; for 3h;
97%	Stage #1: allyl (4-allyloxy)benzoate With sodium hydroxide for 3h; Heating; Stage #2: With hydrogenchloride at 20℃; Further stages.;
95%	With sodium hydroxide In water for 6h; Reflux;

83%

With potassium hydroxide In methanol at 20℃;

Reference： [1]Location in patent: body text Perchyonok, V. Tamara; Ryan, Sarah J.; Langford, Steven J.; Hearn, Milton T.; Tuck, Kellie L. [Synlett, 2008, # 8, p. 1233 - 1235]
[2]Brown, David P.; Duong, Hoan Q. [Journal of Heterocyclic Chemistry, 2008, vol. 45, # 2, p. 435 - 443]
[3]Daniliuc, Constantin G.; Gilmour, Ryan; Neufeld, Jessica; Sarie, Jérôme C.; Thiehoff, Christian [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 15069 - 15075][Angew. Chem., 2020, vol. 132, # 35, p. 15181 - 15187,7]
[4]Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, Roderich D. [ChemMedChem, 2016, p. 1899 - 1903]

52
[ 59434-20-7 ]
[ 27914-60-9 ]
[ 1206883-02-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 4-allyloxybenzoic acid With trifluoroacetic anhydride In dichloromethane at 0℃; Stage #2: 1,3,5-tri-O-benzylphloroglucinol In dichloromethane at 20℃; for 48h;

Reference： [1]Location in patent: experimental part Hendra, Phebe; Fukushi, Yukiharu; Hashidoko, Yasuyuki [Bioscience, Biotechnology and Biochemistry, 2009, vol. 73, # 10, p. 2172 - 2182]

53
[ 27914-60-9 ]
[ 1282613-28-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 1,4-dioxane / 20 - 80 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 2.2: 1.5 h / 20 °C
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 1,4-dioxane / 20 - 80 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C 2.2: 1.5 h / 20 °C

Reference： [1]Current Patent Assignee: ALMIRALL SA - EP2305660, 2011, A1
[2]Current Patent Assignee: ALMIRALL SA - WO2011/35900, 2011, A1

54
[ 27914-60-9 ]
[ 1282613-29-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: trichlorophosphate / 1,4-dioxane / 20 - 80 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 2.2: 1.5 h / 20 °C 3.1: osmium(VIII) oxide; 4-methyl-morpholine / water; <i>tert</i>-butyl alcohol; tetrahydrofuran / 20 °C 3.2: 2 h / 20 °C
	Multi-step reaction with 3 steps 1.1: trichlorophosphate / 1,4-dioxane / 20 - 80 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C 2.2: 1.5 h / 20 °C 3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; <i>tert</i>-butyl alcohol; tetrahydrofuran / 20 °C 3.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: ALMIRALL SA - EP2305660, 2011, A1
[2]Current Patent Assignee: ALMIRALL SA - WO2011/35900, 2011, A1

55
[ 27914-60-9 ]
[ 6610-31-7 ]
[ 1282613-27-7 ]

Yield	Reaction Conditions	Operation in experiment
54%	With trichlorophosphate In 1,4-dioxane at 20 - 80℃;	51 PREPARATION 51 5-(4-(Allyloxy)-phenyl)-N-butyl-1,3,4-thiadiazol-2-amine To a stirred solution of the title compound of Preparation 50 (2.62 g, 14.70 mmol) in dioxane (30 ml), the title compound of preparation 3 (1.97 g, 13.38 mmol) was added portion wise. POCl3 (1.84 ml, 20.10 mmol) was added drop wise and the final mixture was stirred at 80°C for 5h and then at rt overnight. Solvent was removed in vacuum and the solid thus obtained was partitioned between water and dichloromethane. It was basified to pH 8-9 and the organic layer was washed with brine. It was dried and solvent was removed in vacuum to yield a solid that was washed with hexane and ethyl ether. 2.07 g (54% yield) of the title compound were obtained. LRMS: m/z 290 (M+1)+ Retention time: 6.65 min (method B)
54%	With trichlorophosphate In 1,4-dioxane at 20 - 80℃;	51 To a stirred solution of the title compound of Preparation 50 (2.62 g, 14.70 mmol) in dioxane (30 ml), the title compound of preparation 3 (1.97 g, 13.38 mmol) was added portion wise. POCI3 (1.84 ml, 20.10 mmol) was added drop wise and the final mixture was stirred at 80°C for 5h and then at rt overnight. Solvent was removed in vacuum and the solid thus obtained was partitioned between water and dichloromethane. It was basified to pH 8-9 and the organic layer was washed with brine. It was dried and solvent was removed in vacuum to yield a solid that was washed with hexane and ethyl ether. 2.07 g (54% yield) of the title compound were obtained.LRMS: m/z 290 (M+1)+ Retention time: 6.65 min (method B)

Reference： [1]Current Patent Assignee: ALMIRALL SA - EP2305660, 2011, A1 Location in patent: Page/Page column 39-40
[2]Current Patent Assignee: ALMIRALL SA - WO2011/35900, 2011, A1 Location in patent: Page/Page column 59

56
[ 33148-47-9 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 4-allyloxy-benzonitrile With water; sodium hydroxide In ethanol at 20 - 110℃; Sealed; Stage #2: With hydrogenchloride In ethanol; dichloromethane; water	50 PREPARATION 50 4-(allyloxy)-benzoic acid In a sealed tube the title compound of preparation 49 (2.76 g, 17.34 mmol) was suspended in 8 M aqueous NaOH solution (17 ml). Ethanol was added (1ml) and the mixture was stirred at 110°C for 5h and then at rt overnight. Dichloromethane and water were added to the mixture and it was acidified with 6 M HCl to pH 1. Layers were separated and the aqueous one was extracted with dichloromethane twice. The combined organic layers were washed with water and brine, dried and solvent was finally removed in vacuum. The title compound was obtained as a yellow solid (2.62 g, 85% yield). LRMS: m/z 179 (M+1)+ Retention time: 5.42 min (method B)
85%	Stage #1: 4-allyloxy-benzonitrile With sodium hydroxide In ethanol; water at 20 - 110℃; Stage #2: With hydrogenchloride; water In ethanol; dichloromethane	50 In a sealed tube the title compound of preparation 49 (2.76 g, 17.34 mmol) was suspended in 8 M aqueous NaOH solution (17 ml). Ethanol was added (1 ml) and the mixture was stirred at 110°C for 5h and then at rt overnight. Dichloromethane and water were added to the mixture and it was acidified with 6 M HCI to pH 1. Layers were separated and the aqueous one was extracted with dichloromethane twice. The combined organic layers were washed with water and brine, dried and solvent was finally removed in vacuum. The title compound was obtained as a yellow solid (2.62 g, 85% yield).LRMS: m/z 179 (M+1)+

Reference： [1]Current Patent Assignee: ALMIRALL SA - EP2305660, 2011, A1 Location in patent: Page/Page column 39
[2]Current Patent Assignee: ALMIRALL SA - WO2011/35900, 2011, A1 Location in patent: Page/Page column 59

57
[ 97344-30-4 ]
[ 27914-60-9 ]
[ 448933-51-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 30℃; for 24h;

Reference： [1]Location in patent: experimental part Xu, Xiao-Xu; Hong, Zhe; Liu, Fei [Molecular Crystals and Liquid Crystals, 2010, vol. 533, p. 52 - 62]

58
[ 27914-60-9 ]
[ 80806-68-4 ]
[ 1245062-17-2 ]

Yield	Reaction Conditions	Operation in experiment
51%	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 72h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Martinelli, Elisa; Paoli, Francesca; Gallot, Bernard; Galli, Giancarlo [Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 18, p. 4128 - 4139]

59
[ 27914-60-9 ]
[ 83953-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 6 h / 90 °C 2: pyridine / tetrahydrofuran
	Multi-step reaction with 2 steps 1: thionyl chloride / 7 h / 20 - 55 °C 2: pyridine / chloroform / 6 h / 60 °C

Reference： [1]Wu, Xiaojuan; Yu, Lilong; Cao, Hui; Guo, Renwei; Li, Kexuan; Cheng, Zihui; Wang, Feifei; Yang, Zhou; Yang, Huai [Polymer, 2011, vol. 52, # 25, p. 5836 - 5845]
[2]Han, Li; Ma, Hongwei; Li, Yang; Wu, Jian; Xu, Hanyan; Wang, Yurong [Macromolecules, 2015, vol. 48, # 4, p. 925 - 941]

60
[ 27914-60-9 ]
(S)-(-)-1,1'-binaphthyl-2,2'-diyl bis(4-(allyloxy)benzoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 6 h / 90 °C 2: pyridine / tetrahydrofuran / 10 h / 90 °C

Reference： [1]Wu, Xiaojuan; Yu, Lilong; Cao, Hui; Guo, Renwei; Li, Kexuan; Cheng, Zihui; Wang, Feifei; Yang, Zhou; Yang, Huai [Polymer, 2011, vol. 52, # 25, p. 5836 - 5845]

61
[ 106-95-6 ]
[ 99-96-7 ]
[ 27914-60-9 ]
[ 26595-60-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 305 mg 2: 570 mg	With sodium hydroxide In ethanol; water Reflux;	6.6.3.9 Ally 4-(allyloxy)benzoate (17) and 4-(Allyloxy)benzoic acid (18) Allyl bromide (2.5g, 20.7mmol) was added to 4-hydroxybenzoic acid (16) (700mg, 5.07mmol) and NaOH (452mg, 11.3mmol) in 20mL 1:1 H2O/ ethanol (v/v). The solution was heated to reflux overnight, and then solvent was removed under reduced pressure to yield the crude products. Purification was carried out on a silica gel column using hexanes/ ethyl acetate (3:1) to provide the pure compounds 17 (570mg) and 18 (305mg) as colorless solids. Compound 17 (834mg, 3.82mmol) and NaOH (153mg, 3.83mmol) were dissolved in 10mL 1:1 H2O/ethanol (v/v) and the solution was heated to reflux overnight. The solvent was removed under reduced pressure and the solid was dissolved in H2O and acidified. The aqueous solution was extracted with ethyl acetate (3×30mL), and then the organic layer was combined and dried with anhydrous Na2SO4. Compound 18 was obtained and further purified by recrystallization in 1:1 hexanes/ ethyl acetate (650mg, 95%). Compound17: 1H NMR (CDCl3, 300MHz) δ 8.02 (d, J=8.1Hz, 2H), 6.91 (d, J=8.1Hz, 2H), 6.01 (m, 2H), 5.40 (d, J=17.1Hz, 2H), 5.28 (m, 2H), 4.80 (d, J=5.7Hz, 2H), 4.53 (d, J=4.8Hz, 2H). Compound 18: 1H NMR (CDCl3, 300MHz) δ 8.08 (d, J=8.8Hz, 2H), 6.98 (d, J=8.8Hz, 2H), 6.08 (m, 1H), 5.45 (d, J=17.1Hz, 1H), 5.35 (d, J=10.5Hz, 1H), 4.64 (d, J=5.1Hz, 2H).

Reference： [1]Yi, Bitna; Long, Sihui; González-Cestari, Tatiana F.; Henderson, Brandon J.; Pavlovicz, Ryan E.; Werbovetz, Karl; Li, Chenglong; McKay, Dennis B. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4730 - 4743]

62
(S)-allyl 2-(allyloxy)-4-(2-(allyloxy)-4-(4-(2-(4-aminobenzamido)-3-cyanopropanamido)benzamido)-3-methoxybenzamido)-3-methoxybenzoate [ No CAS ]
[ 27914-60-9 ]
(S)-allyl 2-(allyloxy)-4-(2-(allyloxy)-4-(4-(2-(4-(4-(allyloxy)benzamido)benzamido)-3-cyanopropanamido)benzamido)-3-methoxybenzamido)-3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 4-allyloxybenzoic acid With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (S)-allyl 2-(allyloxy)-4-(2-(allyloxy)-4-(4-(2-(4-aminobenzamido)-3-cyanopropanamido)benzamido)-3-methoxybenzamido)-3-methoxybenzoate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;	Compound 7 BTC (1 .15 eq, 0.100 mmol, 30 mg) was dissolved in dry THF (5 ml) under an atmosphere of argon. 4-(Allyloxy)benzoic acid (3.5 eq, 0.305 mmol, 67 mg) was added. syn-Collidine (8 eq, 0.700 mmol, 0.092 ml) was slowly added via syringe and the white suspension was stirred at room temperature for 10 min. The amine (1 eq, 0.087 mmol, 70 mg) and DIPEA (10 eq, 0.872 mmol, 0.150 ml) were added via syringe. The reaction mixture was stirred for 12 h at room temperature and quenched by the addition of water. After removing the organic solvent under reduced pressure the aqueous phase was extracted with EtOAc (3 x 50 ml). The organic phase was washed with saturated NaHC03 solution (2 x 50 ml), aqueous HCI solution (5 %, 2 x 50 ml), water (1 x 50 ml) and brine (1 x 50 ml). After drying over Na2S04 and filtration, the solvent was removed under reduced pressure. Column chromatography (CHCI3:MeOH; 1 .5 % MeOH) yielded the product as an orange oil (58 mg, 69 %). The oil (1 eq, 0.058 mmol, 56 mg) and phenylsilane (8 eq, 0.466 mmol, 0.057 ml) were dissolved in dry THF under an atmosphere of argon and exclusion of light. Pd[P(Ph)3]4 (0.5 eq, 0.029 mmol, 34 mg) was added and the mixture was stirred 12 h at room temperature. After adding 3 drops of acetic acid the solvent was removed under reduced pressure. The product was isolated after preparative HPLC purification as a white powder (19 mg, 41 %). H-NMR (DMSO-ds, 500 MHz): δ [ppm] 3.07 (dd, Ji = 16.65 Hz, J2 = 8.72 Hz, 1 H), 3.16 (m, 1 H), 3.77 (s, 3H), 3.90 (s, 3H), 4.98 (m, 1 H), 6.87 (d, J = 8.52 Hz, 2H), 7.57 (dd, Ji = 8.92 Hz, J2 = 4.56 Hz, 2H), 7.80 (m, 3H), 7.94 (m, 10H), 9.02 (d, J = 7.53 Hz, 1 H), 9.68 (s, 1 H), 10.16 (s, 1 H), 10.23 (s, 1 H), 10.59 (s, 1 H), 1 1 .14 (s, 1 H), 1 1 .52 (s, 1 H). HRMS (ESI): [M+H]+ calculated: 803.2308 found: 803.2323 [M+Na]+ calculated: 825.2127 found: 825.2141
69%	With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: TECHNICAL UNIVERSITY OF BERLIN - WO2014/125075, 2014, A1 Location in patent: Page/Page column 347
[2]Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, Roderich D. [ChemMedChem, 2016, p. 1899 - 1903]

63
[ 27914-60-9 ]
cholesteryl 4-(3-(1,1,3,3-tetramethyldisiloxany)propoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / 7 h / 20 - 55 °C 2: pyridine / chloroform / 6 h / 60 °C 3: platinum⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex / toluene; 5,5-dimethyl-1,3-cyclohexadiene / 60 °C / Inert atmosphere

Reference： [1]Han, Li; Ma, Hongwei; Li, Yang; Wu, Jian; Xu, Hanyan; Wang, Yurong [Macromolecules, 2015, vol. 48, # 4, p. 925 - 941]

64
[ 57-88-5 ]
[ 27914-60-9 ]
[ 83953-73-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
25%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 8h; Reflux;	Cholesteryl 4-(2-propenyloxy)benzoate C 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (EDC, 4.22 g, 2.2×10-2 mol) was added slowly to a stirred solution of 4-(2-propenyloxy)benzoic acid (1.38 g, 7.7×10-2 mol), cholesterol (3.28 g, 8.4 mmol) and N,N-dimethyl-4-aminopyridine (DMAP, 0.24 g, 1.9 mmol) in dry dichloromethane (200 ml). The mixture was refluxed for 8 h and was concentrated under vacuum. The crude product was dissolved in hexane and filtered to remove the insoluble traces. The product was purified by column chromatography (silica gel, dicloromethane) As a result, 1.0 g of cholesteryl 4-(2-propenyloxy)benzoate as colorless crystals. Yield : 1.0 g (25%) 1H-NMR (CDCl3) : δ (ppm) 7.99 (d, J = 8.6 Hz, 2H), 6.92 (d, J = 9.1 Hz, 2H), 6.06 (ddt, J = 17.1 Hz, 10.3 Hz, 5.5 Hz, 1H), 5.46-5.38 (m, 2H), 5.32 (dq, J = 10.5 Hz, 1.4Hz, 1H), 4.86-4.77 (m, 1H), 4.59 (dt, J = 5.5 Hz, 1.4 Hz, 2H) 2.43 (d, J = 7.7 Hz, 2H), 2.04-0.94 (m, 26H), 1.06 (s, 3H), 0.92 (d, J = 6.3 Hz, 3H), 0.870 (d, J = 6.3 Hz, 3H), 0.865 (d, J = 6.3 Hz, 3H), 0.69 (s, 3H).
	With dmap; dicyclohexyl-carbodiimide

With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

Reference： [1]Yao, Wenhuan; Gao, Yanzi; Yuan, Xiao; He, Baofeng; Yu, Haifeng; Zhang, Lanying; Shen, Zhihao; He, Wanli; Yang, Zhou; Yang, Huai; Yang, Dengke [Journal of Materials Chemistry C, 2016, vol. 4, # 7, p. 1425 - 1440]
[2]Katsuki, Kaito; Kaneko, Kosuke; Kaneko, Kimiyoshi; Kato, Riki; Miyamoto, Nobuyoshi; Hanasaki, Tomonori [Journal of Organometallic Chemistry, 2019, vol. 886, p. 34 - 39]
[3]Yao, Wenhuan; Gao, Yanzi; Li, Fasheng; Zhang, Lanying; Yang, Zhou; Yang, Huai [RSC Advances, 2016, vol. 6, # 90, p. 87502 - 87512]
[4]Yao, Wenhuan; Gao, Yanzi; Zhang, Cuihong; Li, Chenyue; Li, Fasheng; Yang, Zhou; Zhang, Lanying [Journal of Polymer Science, Part A: Polymer Chemistry, 2017, vol. 55, # 10, p. 1765 - 1772]

65
[ 27914-60-9 ]
[ 150-76-5 ]
[ 73376-32-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
72%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;	The synthesis of 4-methoxyphenyl 4-(5-hexenyloxy)benzoate (4M) is described as follows: General procedure: 4-(5-Hexenyloxy)benzoic acid (8) (1.6 g, 0.0081 mol) and 4-methoxyphenol (1 g, 0.0081 mol) dissolved in dry dichloromethane (100 mL), N,N-dicyclohexylcarbodiimide (DCC, 2.0 g, 0.0097 mol) and 4-(N,N-dimethylamino)pyridine (DMAP, 0.2 g) were added to react under nitrogen. The reaction mixture was stirred for 24 h at room temperature. The solution was filtered. After removal of the solvent by evaporation under reduced pressure, the residue was purified by recrystallization from ethanol to yield 1.74 g (66 %) of white crystal.
	With dmap; dicyclohexyl-carbodiimide

Reference： [1]Yao, Wenhuan; Gao, Yanzi; Yuan, Xiao; He, Baofeng; Yu, Haifeng; Zhang, Lanying; Shen, Zhihao; He, Wanli; Yang, Zhou; Yang, Huai; Yang, Dengke [Journal of Materials Chemistry C, 2016, vol. 4, # 7, p. 1425 - 1440]
[2]Chen, Cheng-Chih; Lin, Chih-Hung [Asian Journal of Chemistry, 2016, vol. 28, # 6, p. 1270 - 1274]
[3]Yao, Wenhuan; Gao, Yanzi; Li, Fasheng; Zhang, Lanying; Yang, Zhou; Yang, Huai [RSC Advances, 2016, vol. 6, # 90, p. 87502 - 87512]

66
[ 100-02-7 ]
[ 27914-60-9 ]
4-nitrophenyl 4-(allyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 4h;

Reference： [1]Harnoy, Assaf J.; Slor, Gadi; Tirosh, Einat; Amir, Roey J. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5813 - 5819]

67
[ 99-96-7 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 2: potassium hydroxide / methanol / 20 °C
	Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 17.5 h / 40 - 70 °C 1.2: 1 h / 70 °C 2.1: sodium hydroxide / water / 6 h / Reflux

Reference： [1]Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, Roderich D. [ChemMedChem, 2016, p. 1899 - 1903]
[2]Daniliuc, Constantin G.; Gilmour, Ryan; Neufeld, Jessica; Sarie, Jérôme C.; Thiehoff, Christian [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 15069 - 15075][Angew. Chem., 2020, vol. 132, # 35, p. 15181 - 15187,7]

68
[ 27914-60-9 ]
[ 767-00-0 ]
[ 73376-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;

Reference： [1]Yao, Wenhuan; Gao, Yanzi; Zhang, Cuihong; Li, Chenyue; Li, Fasheng; Yang, Zhou; Zhang, Lanying [Journal of Polymer Science, Part A: Polymer Chemistry, 2017, vol. 55, # 10, p. 1765 - 1772]

69
[ 524-38-9 ]
[ 27914-60-9 ]
1,3-dioxoisoindolin-2-yl 4-(allyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 3h; Inert atmosphere;

Reference： [1]Candish, Lisa; Teders, Michael; Glorius, Frank [Journal of the American Chemical Society, 2017, vol. 139, # 22, p. 7440 - 7443]

70
[ 40663-68-1 ]
[ 27914-60-9 ]
1-(allyloxy)-4-isocyanobenzene [ No CAS ]
[ 62-53-3 ]
C₃₆H₃₄N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	Stage #1: 4-(2-propenyloxy)benzaldehyde; aniline In ethanol; 2,2,2-trifluoroethanol for 5h; Inert atmosphere; Molecular sieve; Stage #2: 4-allyloxybenzoic acid; 1-(allyloxy)-4-isocyanobenzene In ethanol; 2,2,2-trifluoroethanol at 20℃; for 72h; Inert atmosphere;

Reference： [1]Lambruschini, Chiara; Galante, Denise; Moni, Lisa; Ferraro, Francesco; Gancia, Giulio; Riva, Renata; Traverso, Alessia; Banfi, Luca; D'Arrigo, Cristina [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9331 - 9351]

71
[ 2769-71-3 ]
[ 95592-67-9 ]
[ 1688-69-3 ]
[ 27914-60-9 ]
C₃₈H₃₈N₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: 4-pivaloyloxybenzaldehyde; p-allyloxyaniline In ethanol; 2,2,2-trifluoroethanol for 5h; Inert atmosphere; Molecular sieve; Stage #2: 2,6-dimethylphenyl isonitrile; 4-allyloxybenzoic acid In ethanol; 2,2,2-trifluoroethanol at 20℃; for 72h; Inert atmosphere;

Reference： [1]Lambruschini, Chiara; Galante, Denise; Moni, Lisa; Ferraro, Francesco; Gancia, Giulio; Riva, Renata; Traverso, Alessia; Banfi, Luca; D'Arrigo, Cristina [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9331 - 9351]

72
1,2-bis(4-(allyloxy)phenyl)ethane-1,2-diol [ No CAS ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; for 12h; Sealed tube;

Reference： [1]Zhou, Zhong-Zhen; Liu, Mingxin; Lv, Leiyang; Li, Chao-Jun [Angewandte Chemie - International Edition, 2018, vol. 57, # 10, p. 2616 - 2620][Angew. Chem., 2018, vol. 130, p. 2646 - 2650,5]

73
[ 27914-60-9 ]
(Z)-4-(cyclopentyloxy)-N’-hydroxybenzimidamide [ No CAS ]
5-(4-(allyloxy)phenyl)-3-(4-(cyclopentyloxy)phenyl)-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: (Z)-4-(cyclopentyloxy)-N’-hydroxybenzimidamide With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50 - 100℃; for 0.25h; Stage #2: 4-allyloxybenzoic acid In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; for 14h;	5-(4-(Allyloxy)phenyl)-3-(4-(cyclopentyloxy)phenyl)-1 ,2,4-oxadiazole (8). Compound 6 (0.62 g, 3.5 mmol) and 1,1’-carbonyldiimidazole (0.53 g, 3.25 mmol) were dissolved in 4 mL DMF at 50 °C. The mixture was stirred for 15 minutes and compound 7(0.55 g, 2.5 mmol) in 15 mL THF was added. The temperature was increased to 100 °C and the reaction was complete after 14 h. The reaction was quenched with saturated NH4C1 solution and was extracted with ethyl acetate (25 mL, 3x). The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified on silica gel chromatography (hexane/ethyl acetate, 50:1) to give the title compound 8 as a viscous oil (0.70 g, 78%). ‘H NIVIR (500 MFIz, CDC13) ö 1.66- 1.60 (m, 2H), 1.97-1.75 (m, 6H), 4.62-4.61 (m, 2H), 4.84-4.82 (m, 1H), 5.34-5.32 (m, 1H),5.46-5.42 (m, 1H), 6.09-6.02 (m, 1H), 6.96 (d, J= 9.0 Hz, 2H), 7.03 (d, J= 9.0 Hz, 2H), 8.06 (d, J 9.0 Hz, 2H), 8.13 (d, J 9.0 Hz, 2H). ‘3C NMR (125 MHz, CDC13) ö 24.3, 33.1,69.2, 79.7, 115.4, 115.9, 117.4, 118.4, 119.3, 129.2, 130.2, 132.7, 160.7, 162.3, 168.8, 175.4; HRMS [M + H], calcd for C22H23N203 363.1703; found 363.1709.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF NOTRE DAME DU LAC - WO2018/49404, 2018, A1 Location in patent: Page/Page column 19; 35; 36

74
[ 67-56-1 ]
[ 27914-60-9 ]
[ 35750-24-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid at 20℃; for 48h;	Sample Preparation General procedure: Samples were prepared in2mLHPLCvials using anAndrewAlliance pipetting robot. The 24 analyte compounds wereprepared in 0.05% H2SO4 in three different solvents (methanol,ethanol, and isopropanol) for esterification to the b, c,and d compounds by adding a few crystals of each analytecompound to the vials and mixing. Dissolved analytes werestored at room temperature for 2 d to allow for esterificationof the carboxylic acid to occur.

Reference： [1]Blincoe, William D.; Rodriguez-Granillo, Agustina; Saurí, Josep; Pierson, Nicholas A.; Joyce, Leo A.; Mangion, Ian; Sheng, Huaming [Journal of the American Society for Mass Spectrometry, 2018, vol. 29, # 4, p. 694 - 703]

75
[ 99-76-3 ]
[ 27914-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / butanone / 24 h / Reflux 2: sodium hydroxide / water; methanol / 1.5 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: sodium hydroxide / water; 1,4-dioxane / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: sodium hydroxide; water / methanol; tetrahydrofuran / 20 °C

Reference： [1]Katsuki, Kaito; Kaneko, Kosuke; Kaneko, Kimiyoshi; Kato, Riki; Miyamoto, Nobuyoshi; Hanasaki, Tomonori [Journal of Organometallic Chemistry, 2019, vol. 886, p. 34 - 39]
[2]Datta, Dhrubajyoti; Debnath, Joy; Franzblau, Scott G.; Ghosh, Kalyan Sundar; Hari, Natarajan; Ma, Rui; Rana, Shiwani; Velappan, Anand Babu [Bioorganic Chemistry, 2020, vol. 103]
[3]Cui, Yingjun; Zhang, Mengyi; Xu, Honglei; Zhang, Tingrong; Zhang, Songming; Zhao, Xiuhe; Jiang, Peng; Li, Jing; Ye, Baijun; Sun, Yuanjun; Wang, Mukuo; Deng, Yangping; Meng, Qing; Liu, Yang; Fu, Qiang; Lin, Jianping; Wang, Liang; Chen, Yue [Journal of Medicinal Chemistry, 2022, vol. 65, # 4, p. 2971 - 2987]

76
[ 381-73-7 ]
[ 27914-60-9 ]
4-(4,4-difluorobutoxy)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrahydrofuran; [bis(acetoxy)iodo]benzene at 50℃; for 14h; Irradiation; regioselective reaction;

Reference： [1]Meyer, Claudio F.; Hell, Sandrine M.; Misale, Antonio; Trabanco, Andrés A.; Gouverneur, Véronique [Angewandte Chemie - International Edition, 2019, vol. 58, # 26, p. 8829 - 8833][Angew. Chem., 2019, vol. 131, # 26, p. 8921 - 8925,5]

77
[ 27914-60-9 ]
4-allyloxy-N-(4-(4-(((2S,4R)-2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dmap / N,N-dimethyl-formamide / 0.25 h 1.2: 12 h / 20 °C 2.1: caesium carbonate / 4 h / 60 °C

Reference： [1]Wen, Jiachen; Chennamadhavuni, Divya; Morel, Shana R.; Hadden, M. Kyle [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 9, p. 1290 - 1295]

78
[ 27914-60-9 ]
4-hydroxy-N-(4-(4-(((2S,4R)-2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dmap / N,N-dimethyl-formamide / 0.25 h 1.2: 12 h / 20 °C 2.1: caesium carbonate / 4 h / 60 °C 3.1: sodium tetrahydroborate; iodine / tetrahydrofuran / 0 - 20 °C

Reference： [1]Wen, Jiachen; Chennamadhavuni, Divya; Morel, Shana R.; Hadden, M. Kyle [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 9, p. 1290 - 1295]

79
[ 56621-48-8 ]
[ 27914-60-9 ]
4-allyloxy-N-(4-(4-hydroxyphenyl)piperazin-1-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 4-allyloxybenzoic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide for 0.25h; Stage #2: 1-(4-hydroxyphenyl)piperazine In N,N-dimethyl-formamide at 20℃; for 12h;

Reference： [1]Wen, Jiachen; Chennamadhavuni, Divya; Morel, Shana R.; Hadden, M. Kyle [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 9, p. 1290 - 1295]

80
[ 719-98-2 ]
[ 27914-60-9 ]
S-(trifluoromethyl) 4-(allyloxy)benzothioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With iron(III) chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Mao, Runze; Bera, Srikrishna; Cheseaux, Alexis; Hu, Xile [Chemical Science, 2019, vol. 10, # 41, p. 9555 - 9559]

81
[ 384-64-5 ]
[ 27914-60-9 ]
1-(4-(allyloxy)phenyl)-4,4-difluoro-3-phenylbut-3-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 48h; Molecular sieve; Inert atmosphere; Sealed tube; Irradiation;

Reference： [1]Guo, Yuan-Qiang; Wang, Ruiguo; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Organic Letters, 2020, vol. 22, # 2, p. 709 - 713]

82
[ 27914-60-9 ]
[ 6638-79-5 ]
4-(allyloxy)-N-methoxy-N-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 4-allyloxybenzoic acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; chemoselective reaction;	General procedure for the synthesis of Weinreb amides General procedure: A. To a mixture of benzoic acid (50 mg, 0.41 mmol, 1 equiv), PPh3 (160 mg, 0.61 mmol, 1.5 equiv) and NBS (108.5 mg, 0.61 mmol, 1.5 equiv), CH2Cl2 (2 ml) was added and the reaction was stirred at 0 °C for 15 min. The reaction was brought to room temperature and N,O-dimethylhydroxylamine hydrochloride (59.5 mg, 0.61 mmol, 1.5 equiv) and Et3N (45.5 mg, 63 µl, 0.45 mmol, 1.1 equiv) were added and reaction was stirred for 1 h at room temperature. The reaction mixture was quenched with aqueous sodium bicarbonate solution and diluted with CH2Cl2. The bicarbonate washings were again extracted with CH2Cl2 and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. Column chromatography was performed using EtOAc/Petroleum ether (1:5).

Reference： [1]Pilathottathil, Fathima; Vineet Kumar, Doppalapudi; Kaliyamoorthy, Alagiri [Synthetic Communications, 2020, vol. 50, # 11, p. 1622 - 1632]

83
[ 27914-60-9 ]
N'-(4-(allyloxy)benzoyl)-3,4,5-trimethoxybenzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / benzene / Reflux 2: triethylamine / N,N-dimethyl-formamide / 20 °C

Reference： [1]AbdelHafez, El-Shimaa M. N.; Abdelhamid, Dalia; Aly, Omar M.; Maklad, Raed M. [Bioorganic Chemistry, 2020, vol. 99]

84
[ 27914-60-9 ]
1-(4-(allyloxy)phenyl)-2-phenylethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloromethane / 12 h / 20 °C / Inert atmosphere 2: caesium carbonate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 1,4-dimethyl-1,2,4-triazolium iodide / acetonitrile / 20 °C / Inert atmosphere; Irradiation; Sealed tube

Reference： [1]Betori, Rick C.; Davies, Anna V.; Fitzpatrick, Keegan P.; Scheidt, Karl A. [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 9143 - 9148][Angew. Chem., 2020, vol. 132, # 23, p. 9228 - 9233,6]

85
[ 27914-60-9 ]
[ 530-62-1 ]
C₁₃H₁₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃; for 12h; Inert atmosphere;

Reference： [1]Betori, Rick C.; Davies, Anna V.; Fitzpatrick, Keegan P.; Scheidt, Karl A. [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 9143 - 9148][Angew. Chem., 2020, vol. 132, # 23, p. 9228 - 9233,6]

86
[ 13552-31-3 ]
[ 27914-60-9 ]
C₁₃H₁₇NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 4-allyloxybenzoic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3-Amino-1,2-propanediol In N,N-dimethyl-formamide at 20℃;	5 Compound 2 (2.49g, 14mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCL) (2.68g, 14mmol), N-hydroxysuccnnimide (NHS) (1.61 g, 14 mmol) was dissolved in DMF, and after stirring at room temperature for 1 h, compound 3 (1.4 g, 15.4 mmol) was added, and the reaction was continued at room temperature overnight. The solvent of the reaction solution was evaporated under reduced pressure, and the obtained residue was column chromatographed to obtain compound 4 (2.81 g, yield 82%)

Reference： [1]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN111454288, 2020, A Location in patent: Paragraph 0133; 0136-0137

87
[ 27914-60-9 ]
[ 100-83-4 ]
3-formylphenyl 4-(allyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.9%	Stage #1: 4-allyloxybenzoic acid; meta-hydroxybenzaldehyde With dmap In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;	4.3.5 General procedure for the synthesis of aldehyde scaffolds 7a-7n and 8a-8n General procedure: 3-Hydroxybenzaldehyde (for 7a-7n) or 4-hydroxybenzaldehyde (for 8a-8n) (1.0g, 8.19mmol), DMAP (0.05g, 0.4mmol) and the corresponding 4-alkoxy benzoic acid (8.19mmol) were dissolved in DMF and stirred at room temperature for 15min. Then DCC (2.0g, 9.83mmol) was added drop wise to the reaction mixture. After completion of reaction, the reaction mixture was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water and brine solution. The organic portion was dried over sodium sulfate and concentrated under reduced pressure. The crude was then purified by column chromatography (silica gel 100-200 mesh) using ethyl acetate in hexanes to obtain the product.

Reference： [1]Datta, Dhrubajyoti; Debnath, Joy; Franzblau, Scott G.; Ghosh, Kalyan Sundar; Hari, Natarajan; Ma, Rui; Rana, Shiwani; Velappan, Anand Babu [Bioorganic Chemistry, 2020, vol. 103]

88
[ 27914-60-9 ]
3-(benzo[d]thiazol-2-yl)phenyl 4-(allyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dmap / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 20 °C 2.1: 0.08 h 2.2: 0.08 h

Reference： [1]Datta, Dhrubajyoti; Debnath, Joy; Franzblau, Scott G.; Ghosh, Kalyan Sundar; Hari, Natarajan; Ma, Rui; Rana, Shiwani; Velappan, Anand Babu [Bioorganic Chemistry, 2020, vol. 103]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	27914-60-9	MDL No. :	MFCD00526542
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DYDWKSVZHZNBLO-UHFFFAOYSA-N
M.W :	178.19	Pubchem ID :	460690
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 27914-60-9 ] {[proInfo.proName]}

Quality Control of [ 27914-60-9 ]

Related Doc. of [ 27914-60-9 ]

Product Details of [ 27914-60-9 ]

Safety of [ 27914-60-9 ]

Application In Synthesis of [ 27914-60-9 ]

[ 27914-60-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 27914-60-9 ]

Aryls

Alkenes

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 27914-60-9 ] {[proInfo.proName]}

Quality Control of [ 27914-60-9 ]

Related Doc. of [ 27914-60-9 ]

Product Details of [ 27914-60-9 ]

Safety of [ 27914-60-9 ]

Application In Synthesis of [ 27914-60-9 ]

[ 27914-60-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 27914-60-9 ]

Aryls

Alkenes

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 27914-60-9 ]