Name: 96251-92-2|(E)-Ethyl 3-(3-hydroxyphenyl)acrylate|95%
Brand: Ambeed
SKU: A1517990
Rating: 92 (26 reviews)

1
[ 64-17-5 ]
[ 14755-02-3 ]
[ 96251-92-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid for 12h; Reflux;
100%	With sulfuric acid for 6h; Reflux;
97%	With sulfuric acid for 7h; Heating;

97%	With hydrogenchloride In diethyl ether for 48h; Heating;
88%	With sulfuric acid at 20℃; for 21h; Reflux;	1 Production of (E)-Ethyl 343-hydroxyphenyl)aci’ylate (1) To a stirred solution of (E)-3-(3-hydroxyphenyl)acrylic acid (60 70 g, 370 0 mmol) in ethanol (600 mL) was added concentrated sulfuric acid (6 mL) and the reaction mixture heated at reflux for 3 hours, and then at ambient temperature for 1 hours The ethanol was removed by rotary evaporation and the residue partitioned between water and ethyl acetate, The layers were separated and the organic phase washed with saturated sodium bicarbonate solution and brine and concentrated to dryness. The hot oil was then triturated with dichloromethane and beptane. The resultant solid was collected by filtration to give (E)-ethyl 3-(3-hydroxyphenyl)acrylate (1) (62 77 g 88%) as beige solid mp 63 8 -652 °C, H NMR (400 MHz, CDCl) 6 7 74 (d, 1H 16 Hz), 735(m, IH), 7 19(d, IH, J76 Hz), 714 (m, IH), 699 (m, IH), 51 (d,IH, 16 Hz),5.97 (brs, IH), 4.38(q, 2H, J7.1 Hz), 1.44(t, 3H, J7.1 Hz).
	With sulfuric acid
	With thionyl chloride for 24h; Reflux;	4.1.1. General procedure for the preparation of (E)-ethyl (3-(substituted-2-yl) methoxy) phenyl acrylate (1a-f, method 1 as shown in Scheme 1) General procedure: To an icy solution of hydroxy cinnamic acid (10 mmol) in ethanol (30 mL) was added thionyl chloride (0.5 mL) dropwise. The reaction mixture was refluxed for 24 h to give the corresponding crude ethyl cinnamate.
	With sulfuric acid for 12h; Reflux;	3.2. General Method for Synthesizing Compounds 5-12 General procedure: Ferulic acid (1) or trans-4-hydroxycinnamic acid (2) or isoferulic acid (3) or trans-3-hydroxycinnamic acid (4) and five drops of H2SO4 (95%) were refluxed in methanol or ethanol for 12 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with a 5% aqueous NaHCO3 solution and water. After drying over anhydrous Na2SO4,the ethyl acetate was removed in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether mixtures as eluents to afford compounds 5-12.

Reference： [1]Location in patent: experimental part Deng, Jing; Feng, Enguang; Ma, Sheng; Zhang, Yan; Liu, Xiaofeng; Li, Honglin; Huang, Huang; Zhu, Jin; Zhu, Weiliang; Shen, Xu; Miao, Liyan; Liu, Hong; Jiang, Hualiang; Li, Jian [Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4508 - 4522]
[2]Gunesch, Sandra; Soriano-Castell, David; Lamer, Stephanie; Schlosser, Andreas; Maher, Pamela; Decker, Michael [ACS Chemical Neuroscience, 2020, vol. 11, # 22, p. 3823 - 3837]
[3]Guanti, Giuseppe; Banfi, Luca; Riva, Renata [Tetrahedron, 1994, vol. 50, # 41, p. 11945 - 11966]
[4]Orr, G. Faye; Musso, David L. [Synthetic Communications, 1996, vol. 26, # 1, p. 179 - 189]
[5]Current Patent Assignee: ACCUGEN; VECTUS BIOSYSTEMS LIMITED - WO2016/145478, 2016, A1 Location in patent: Paragraph 0086
[6]Nee, Michael W.; Kim, Chongwoo A.; Garg, Sandhya; Griffith, Michael C.; Mizoue, Laura S.; et al. [Tetrahedron Letters, 1988, vol. 29, # 42, p. 5345 - 5348]
[7]Location in patent: experimental part Chen, Hongfei; Li, Guoning; Zhan, Peng; Liu, Xinyong [European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5609 - 5615]
[8]Li, Yang; Feng, Ling; Song, Zhi-Fang; Li, Hai-Bei; Huai, Qi-Yong [Molecules, 2016, vol. 21, # 2]

2
[ 96251-92-2 ]
[ 34708-60-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen In ethanol; water for 1h; Autoclave;	1 Production of Ethy/ 3-(3-hydr oxyphenyQpropanoate (2) (E)-Ethyl 3-(3-hvdroxyphenyl)acrylate (1) (2 2 g 326 0 mmol) and 10% palladium on carbon (50% wt water) in ethanol (260 rnL) was stirred in an autoclave at 140 psi of hydrogen for 1 hour, in 3 batches. The 3 batches were combined, filtered through Celite, washing thoroughly with ethanol. The filtrate was concentrated to give ethyl 3-(3-hydroxyphenyl)propanoate (2) as a pale tan oil (63 23 g, 100%) ‘H NMR (400 MHz, CDCI3) ö 7.23 (m, IH), 6.82 (br 5. 1H), 6.85- 620 (rn, 3Ff), 424 (q, 2H, J 71 Hz), 3.00 it. 2H, J 7.5 Hz), 2.72 It, 2H, J 75 Hz), 1.34 it, 3H, J 7.1 Hz).
98%	With hydrogen In ethanol for 20h; Ambient temperature;
89%	With hydrogen In ethanol for 18h;

	With hydrogen
	With palladium 10% on activated carbon; hydrogen In ethyl [2]alcohol for 12h;	27.2 (E) -3- (3-hydroxyphenyl) acrylic acid ethyl ester 27b (500 mg, 2.60 mmol) was dissolved in 20 mg ethanol, palladium on carbon (50 mg, 10%) was added, the hydrogen was replaced three times and the reaction was stirred for 12 hours.Filtered and the filtrate was concentrated under reduced pressure to give the crude title product ethyl 3- (3-hydroxyphenyl) propionate 27c (470 mg, yellow oil) which was subjected to the next reaction without purification.

Reference： [1]Current Patent Assignee: ACCUGEN; VECTUS BIOSYSTEMS LIMITED - WO2016/145478, 2016, A1 Location in patent: Paragraph 0087
[2]Guanti, Giuseppe; Banfi, Luca; Riva, Renata [Tetrahedron, 1994, vol. 50, # 41, p. 11945 - 11966]
[3]Orr, G. Faye; Musso, David L. [Synthetic Communications, 1996, vol. 26, # 1, p. 179 - 189]
[4]Nee, Michael W.; Kim, Chongwoo A.; Garg, Sandhya; Griffith, Michael C.; Mizoue, Laura S.; et al. [Tetrahedron Letters, 1988, vol. 29, # 42, p. 5345 - 5348]
[5]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - CN103030646, 2016, B Location in patent: Paragraph 0539; 0541; 0546-0548

3
[ 867-13-0 ]
[ 100-83-4 ]
[ 96251-92-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In toluene at 20℃; for 48h;
80%	Stage #1: meta-hydroxybenzaldehyde With sodium ethanolate In toluene at 25℃; for 0.25h; Inert atmosphere; Stage #2: diethoxyphosphoryl-acetic acid ethyl ester In toluene for 0.1h; Microwave irradiation;

Reference： [1]Villieras, Jean; Rambaud, Monique; Graff, Micheline [Tetrahedron Letters, 1985, vol. 26, # 1, p. 53 - 56]
[2]Location in patent: experimental part Bera, Rabin; Dhananjaya; Singh, Shambu Nath; Kumar, Rajender; Mukkanti; Pal, Manojit [Tetrahedron, 2009, vol. 65, # 7, p. 1300 - 1305]

4
[ 54848-86-1 ]
[ 96251-92-2 ]
[ 180071-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide 1.) DMSO, 90 deg C, 30 min, 2.) DMSO, 90 deg C, 5 h; Yield given. Multistep reaction;

Reference： [1]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

5
[ 591-20-8 ]
[ 140-88-5 ]
[ 96251-92-2 ]

Yield	Reaction Conditions	Operation in experiment
77.3%	With palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;	27.1 (E)-3-(3-hydroxyphenyl)acrylic acid ethyl ester 3-bromophenol 27a (3.46 g, 20.0 mmol), palladium acetate (220 mg, 1 mmol), triphenylphosphine (1.05 g, 4 mmol) was dissolved in 50 mL of N, N-dimethylformamide, an additional amount of ethyl acrylate (6.0 g, 60 mmol) and triethylamine (7.07 g, 70 mmol) were added and the temperature was raised to 100 ° C and the reaction was stirred for 12 hours.The organic phase was washed successively with water (50 mL of X3) and saturated sodium chloride solution (50 mL of X3), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The organic layer was washed with silica gel Column chromatography The resulting residue was purified with eluent system B to give the title product (E) -3- (3-hydroxyphenyl) acrylic acid ethyl ester 27b (2.97 g, yellow solid), yield: 77.3%.
24%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 100℃;

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - CN103030646, 2016, B Location in patent: Paragraph 0539; 0541-0544
[2]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

6
[ 626-02-8 ]
[ 140-88-5 ]
[ 96251-92-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 100℃; for 24h;

Reference： [1]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

7
[ 96251-92-2 ]
[ 180071-79-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) K₂CO₃, 2.) KI / 1.) DMSO, 90 deg C, 30 min, 2.) DMSO, 90 deg C, 5 h 2: 90 percent / H₂ / Pd/C / methanol / 10 h / Ambient temperature

Reference： [1]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

8
[ 96251-92-2 ]
2-<3-<((2-methylphenyl)dimethylsilyl)methoxy>benzyl>-8,8-dimethyl-non-4-ene-6-yne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 1.) K₂CO₃, 2.) KI / 1.) DMSO, 90 deg C, 30 min, 2.) DMSO, 90 deg C, 5 h 2: 90 percent / H₂ / Pd/C / methanol / 10 h / Ambient temperature 3: 1.) lithium diisopropylamide / 1.) THF, -70 deg C, 1 h, 2.) hexamethylphosphorotriamide, -70 deg C -> r.t. 4: 90 percent / LiAlH₄ / diethyl ether / 2 h 5: 100 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / Ambient temperature 6: 85 percent / LiAlH₄ / tetrahydrofuran / 4 h / -10 °C

Reference： [1]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

9
[ 96251-92-2 ]
[ 180071-76-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) K₂CO₃, 2.) KI / 1.) DMSO, 90 deg C, 30 min, 2.) DMSO, 90 deg C, 5 h 2: 90 percent / H₂ / Pd/C / methanol / 10 h / Ambient temperature 3: 1.) lithium diisopropylamide / 1.) THF, -70 deg C, 1 h, 2.) hexamethylphosphorotriamide, -70 deg C -> r.t. 4: 90 percent / LiAlH₄ / diethyl ether / 2 h

Reference： [1]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

10
[ 96251-92-2 ]
[ 1027646-67-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) K₂CO₃, 2.) KI / 1.) DMSO, 90 deg C, 30 min, 2.) DMSO, 90 deg C, 5 h 2: 90 percent / H₂ / Pd/C / methanol / 10 h / Ambient temperature 3: 1.) lithium diisopropylamide / 1.) THF, -70 deg C, 1 h, 2.) hexamethylphosphorotriamide, -70 deg C -> r.t.

Reference： [1]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

11
[ 96251-92-2 ]
[ 180071-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) K₂CO₃, 2.) KI / 1.) DMSO, 90 deg C, 30 min, 2.) DMSO, 90 deg C, 5 h 2: 90 percent / H₂ / Pd/C / methanol / 10 h / Ambient temperature 3: 1.) lithium diisopropylamide / 1.) THF, -70 deg C, 1 h, 2.) hexamethylphosphorotriamide, -70 deg C -> r.t. 4: 90 percent / LiAlH₄ / diethyl ether / 2 h 5: 100 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

Reference： [1]Gotteland, Jean-Pierre; Guilhem, Marie-Christine; Halazy, Serge [Synthetic Communications, 1996, vol. 26, # 15, p. 2925 - 2934]

12
[ 96251-92-2 ]
[ 7116-39-4 ]