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Product Details of [ 40663-68-1 ]

CAS No. :	40663-68-1	MDL No. :	MFCD00014133
Formula :	C₁₀H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TYNJQOJWNMZQFZ-UHFFFAOYSA-N
M.W :	162.19	Pubchem ID :	95942
Synonyms :

Safety of [ 40663-68-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280	UN#:
Hazard Statements:	H317	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40663-68-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 40663-68-1 ]
Downstream synthetic route of [ 40663-68-1 ]

[ 40663-68-1 ] Synthesis Path-Upstream 1~3

1
[ 40663-68-1 ]
[ 5736-85-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen In methanol at 20℃; for 2 h;	General procedure: The mixture of the substrate (0.250 mmol), 0.5percent Pd/MS3A or 0.5percent Pd/MS5A (10 wt percent of the substrate) and MeOH (1 mL) was stirred under H₂ atmosphere (balloon) at room temperature. After a given period, the reaction mixture was filtered through a membrane filter (Millipore, Millex^.(R).-LH, 0.45 mm), and the filtrate was concentrated in vacuo to produce the corresponding reduced product.

Reference： [1] Synthetic Communications, 2007, vol. 37, # 24, p. 4381 - 4388
[2] Tetrahedron, 2012, vol. 68, # 39, p. 8293 - 8299
[3] Tetrahedron, 2006, vol. 62, # 51, p. 11925 - 11932
[4] RSC Advances, 2016, vol. 6, # 57, p. 52495 - 52499
[5] Organometallics, 2010, vol. 29, # 9, p. 2098 - 2103
[6] Organic Process Research and Development, 2012, vol. 16, # 6, p. 1230 - 1234

2
[ 40663-68-1 ]
[ 10035-16-2 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755

3
[ 123-08-0 ]
[ 109-64-8 ]
[ 40663-68-1 ]
[ 3722-80-3 ]
[ 17954-81-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate In acetonitrile at 20 - 60℃; for 3 - 4 h; Industry scale	The exemplary process of the invention is shown schematically in Figure 1.0 Step (a): 4-(3-Bromopropyloxy)benzaldehyde (Compound 1)A dry Belatech glass reactor (30L) was flushed with argon and charged with 4- hydroxybenzaldehyde (588g, 4.8MoIe), 1,3-dibromopropane (4.976kg, 24.6MoIe) and anhydrous acetonitrile (24L) under argon. Dried powdered 5 potassium carbonate (1.66kg, 12MoIe) was added in portions to the stirred solution. The suspension was stirred at 55-60°C and monitored by gas chromatography and cooled (ice bath) to room temperature as soon as the 4- hydroxybenxaldehyde had been consumed (3-4hr). Solids were removed by filtration (2L Buechner funnel) and washed with dry acetonitrile (3 x 300 mL). ,0 The combined solvents were reduced in volume by rotary evaporation (bath temperature 40⁰C) and then the excess of 1,3-dibromopropane was removed by <n="21"/>high, vacuum distillation (bath temperature 40⁰C). Crude product was obtained as a bright yellow oil (1350g). The crude product was purified by column chromatography under argon using 10 kg silica gel, eluting with a mixture of heptane:ethyl acetate (75L; 9:1, by vol.) followed by a mixture of heptane: ethyl acetate (HL; 4:1, by vol.). After 5OL of the first eluant had been eluted, fractions (50OmL) of eluate were collected and their purities checked by TLC. The fractions containing pure product were combined and dried by rotary evaporation (bath temperature 4O⁰C) to yield pure product as a colourless oil. Yield: 90Og (3.7MoIe, 77percent). TLC: Rf = 0.38 (A). GC: purity > 95 percent (rt = 12.7min). ¹H-NMR analysis: δ_H (300MHz₅ CD₃OD): 2.35 (quint, ³J Iληz, 2H), 3.58 (t, ³J 7.4Hz, 2H), 4.18 (t, ³J 7.4Hz, 2H), 6.95, 7.85 (2 x d, ³J 8.5Hz; 4H), 9.85 (s, IH).Comments:Acetone and THF as reaction solvents were also investigated and found to give inferior outcomes to acetonitrile.It is important to secure highly pure product in this step. Product contaminated with the elimination product leads in the next step to the corresponding porphyrin by-product containing an unsaturated propene group.The product is air sensitive. Formation of the oxidation product (the carboxylic acid) was observed during workup. Due to the air sensitivity of the product, column chromatography should be carried out under an argon atmosphere and the bottles of the collected fractions should be kept closed.Two main by-products, an elimination product and a dimer, formed in the reaction. By TLC analysis, three compounds were observed: 4-allyloxy- benzaldehyde (R_f - 0.42), product (R_f = 0.38) and 4-[3-(4- foπnylphenoxy)propyloxy]benzaldehyde (R_f= 0.20). <n="22"/>By GC analysis four compounds were detected: excess 1,3-dibromopropane (rt = 4.525min); elimination product (rt = 9.725min); product (rt = 12.858min) and the dimer (rt = 19.75min).

Reference： [1] Patent: WO2007/74340, 2007, A1, . Location in patent: Page/Page column title page; 18-20; Sheet 1/2

[ 40663-68-1 ] Synthesis Path-Downstream 1~20

1
[ 123-08-0 ]
[ 106-95-6 ]
[ 40663-68-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In propan-2-one at 65℃;	1.1 Synthesis of the allyl oxy cinnamate norbornene(Formula 8) monomer1-(1): Synthesis of allyl oxy benzaldehyde; After 4-hydroxy benzaldehyde (20 g, 0.164 mol) was dissolved in 200 mi of acetone, allyl bromide (30 g, 0.246 mol) and K2CO3 (34g, 0.246 mol) were added, and the refluxing was performed at 650Covernight. Next, the resulting mixture was cooled to normaltemperature, and the filtering was performed by using acetone. Thefiltrate was extracted by using ethyl acetate and then subjected towork-up to obtain 27.1 g of the yellow oil product. The amount wasan amount that exceeds the yield of 100%. Even though a smallamount of impurity was present, the subsequent reaction was performed in an oil state.
100%	With N,N,N-tributyl-1-butanaminium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;	19 phenyl N- [4-(prop-2-en-l -yloxy)phenyl]methyl} carbamate 4-(hydroxy)-benzaldehyde (10.0 g, 80.25 mmol), potassium carbonate (163.8 mmol, 22.6 g), tetrabutyl ammonium iodide (1.0 mmol, 377 mg), allyl bromide (121 mmol, 10.6 ml) and N,N-dimethylformamide (4.0 ml) were stirred at 20 °C for 6 hours and then partitioned between water and diethyl ether. The organic phase was washed with water several times, then dried and evaporated to give 4-(allyloxy)-benzaldehyde as an oil (13.3 g, 100 %). This material (11.17 g, 68.8 mmol) was dissolved in ethanol (40 ml) and sodium borohydride (35 mmol, 1.351 g) was added in portions. The mixture was stirred 1 hour and then concentrated, sodium hydroxide (aqueous, 5 M, 30 ml) and water (100 mL) were added and the mixture was extracted with diethyl ether. The organic phase was washed with water and brine and then evaporated to give 4-(allyloxy)-benzylalcohol (10.49 g, 63.9 mmol, 93 %). This alcohol (3.0 g, 18.2 mmol) was dissolved in dichloromethane (10 ml) and thionyl chloride (37 mmol, 2.8 ml) was added. The mixture was stirred at 40 °C for 10 min and then evaporated. The residue was dissolved in N,N-dimethylformamide (7 ml) and potassium phthalimide (20 mmol, 3.75 g) followed by pyridine (5 mmol, 410 μ) were added. The mixture was stirred at room temperature 20 hours and then at 50 °C for 30 min. Hydrochloric acid (aqueous, 1 M, 20 ml) was added. The crystals were isolated by filtration, washed with 33 % methanol in water and dried to give 5.18 g material which was recrystallized from 95 % ethanol to give the phthalimide derivative (4.7 g, 88 % yield). This material was stirred in 33 % methylamine in ethanol (16 ml) and ethanol (15 ml) for 18 hours, then at 60 °C for 30 min. The mixture was partitioned between diethyl ether and sodium hydroxide (0.2 M). The organic phase was separated and extracted with hydrochloric acid (aqueous, 1 M). The aqueous phase was made basic with sodium hydroxide (5 M), then extracted with diethyl ether. The organic phase was dried and evaporated to give the intermediate 4-allyloxy-benzylamine (2.247 g, 86 %). This material (1.5 g, 9.1 mmol) and pyridine (11.83 mmol, 0.96 mL) were stirred in dichloromethane (10 ml) on an ice bath and phenyl chloroformate (10.01 mmol, 1.614 g, 1.3 ml) dissolved in dichloromethane (5 ml) was added dropwise during 20 minutes. The mixture was stirred at room temperature for 1 hour, then partitioned between dichloromethane and hydrochloric acid (aqueous, 0.5 M). The organic phase was dried and evaporated to an oil (2.3 g). Recrystallization from ethanol/water gave the desired intermediate as crystals (4.62 mmol, 1.31 g, 51 %).
100%	With N,N,N-tributyl-1-butanaminium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;	Intermediate 25: [4-(prop-2-en-l-yloxy)phenyl]methanol 4-Hydroxybenzaldehyde (10.0 g, 80.25 mmol), potassium carbonate (163.8 mmol, 22.6 g), tetrabutylammonium iodide (1.0 mmol, 377 mg), allyl bromide (1.5 eq., 121 mmol, 10.6 ml) and N,N-dimethylformamide (4.0 ml) were stirred at 20 °C for 6 hours and then partitioned between water and diethyl ether. The organic phase was washed with water several times, then dried and evaporated to give 4-(allyloxy)benzaldehyde as an oil (13.3 g, 100 %). This material (11.17 g, 68.8 mmol) was dissolved in ethanol (40 ml) and sodium borohydride (35 mmol, 1.351 g) was added in portions. The mixture was stirred 1 hour and then concentrated. Sodium hydroxide (5M, 30 ml) and water (100 ml) were added and the mixture was extracted with diethyl ether. The organic phase was washed with water and brine and then evaporated to give [4-(prop-2-en-l-yloxy)phenyl]methanol (10.49 g, 93 %).

99%	With potassium carbonate In propan-2-one at 20℃; Sealed tube; Inert atmosphere; Reflux;
98%	With Cs₂CO₃; potassium iodide In N,N-dimethyl-formamide at 60℃; for 2h;	General procedure for allyl protection of 10-13 and 18-21 General procedure: To a stirred suspension of acetophenone (1 mmol), Cs2CO3 (3.0 mmol) and KI (0.2 mmol) in anhydrous DMF (8 mL) was added allyl bromide (2.5 mmol) at room temperature. The mixture was stirred at 60 oC for 5 h. After completion of the reaction, cooled to room temperature and neutralized with 2N HCl and diluted with ether (50 mL) and cold water (30 mL). Two layers separated and the aqueous layer was extracted with ether (2 x 40 mL). The combined organic layer was washed with brine (3 x 40 mL), H2O (2 x 40 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography (EA/hexane = 1/20 to 1/5) to afford the pure product. [note: Cs2CO3 (1.5 mmol), KI (0.1 mmol) and allyl bromide (1.2 mmol) were employed in the case of aromatic aldehydes 18-21 (1 mmol) and the reaction was completed in 2 h.].
97%	With potassium carbonate In propan-2-one Heating;
96%	With N,N,N-tributyl-1-butanaminium iodide; sodium hydride In tetrahydrofuran
95%	With potassium carbonate In methanol at 20℃; for 4h;
95%	With potassium carbonate In propan-2-one at 20℃; for 4h; Reflux;
94%	With potassium carbonate In propan-2-one for 18h; Inert atmosphere; Reflux;
94%	With potassium carbonate In propan-2-one at 0 - 20℃; for 60h;	Intermediate D: 4-( allyloxy)benz aldeh deA solution of allyl bromide (5.94 mL, 68.78 mmol) in acetone (20 mL) was added, over a period of 20 min, to a mixture of 4-hydroxybenzaldehyde (8.00 g, 65.50 mmol) and K2C03 (9.96 g, 72.06 mmol) in acetone (100 mL) cooled at 0 °C. The mixture was allowed to reach room temperature and stirred for 60 h . After removal of the solvent, the crude residue was dissolved in EtOAc (100 mL) and washed twice with a mixture of water (100 mL) and NaOH (10% aqueous solution , 10 mL). The organic layer was dried over anhydrous Na2S04 and filtered. After removal of the solvent, 10.00 g of 4-(allyloxy)benzaldehyde were obtained [Rf= 0.5 (10% EtOAc/Hexanes), pale brown oil, 94% yield]
94%	Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate; potassium iodide In ethanol at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 3-bromo-1-propene In ethanol at 80℃; Inert atmosphere;
93.5%	Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate In ethanol at 20℃; for 0.5h; Stage #2: 3-bromo-1-propene In ethanol at 80℃; for 72h; Inert atmosphere;	1 Experimental steps: Add p-hydroxybenzaldehyde (100 mmol) to 50 ml of absolute ethanol, and add anhydrous potassium carbonate (150 mmol) at room temperature for 30 min.Bromopropene (120 mmol) was added dropwise under a nitrogen atmosphere.The molar ratio of p-hydroxybenzaldehyde to bromopropene to anhydrous potassium carbonate is 1:1.2:1.5. After the addition is completed, the temperature is gradually raised to 80 ° C, condensed and refluxed, reacted for 72 hours, filtered, and the solvent is removed under reduced pressure distillation. It was diluted with a small amount of water and extracted with ethyl acetate and brine. The organic phase was combined, anhydrous sodium sulfate was added, and the mixture was allowed to stand overnight, and the silica gel was collected in a dry manner. The mixture was separated by a mixed solvent of petroleum ether/ethyl acetate (volume ratio: 6:1) as an eluent, and the vacuum was separated at 50 ° C. After drying, 15.16 g of the alkenal monomer 4-allyloxybenzaldehyde was obtained in a yield of 93.5%, a pale yellow liquid.
92%	With potassium carbonate In propan-2-one at 20℃; Reflux;
92%	With potassium hydroxide In propan-2-one at 25℃; for 18h;	2.1 Example 2 (1) At room temperature,Combine potassium hydroxide (0.5mol) with p-hydroxybenzaldehyde (1mol),Dissolved in acetone (15mol), after adding allyl bromide (1.3mol),Adjust the temperature to 25°C, and after a period of reaction (18h),The reaction was complete as monitored by TLC.The reaction was quenched with deionized water;Extract at least three times with ethyl acetate, combine the organic phases,dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure,Use petroleum ether and ethyl acetate (V/V) mixed solvent volume ratio to be 8:1 as mobile phase, carry out column chromatography,Product 1 was obtained, yield: 92%.
91%	With potassium carbonate In ethanol Heating;
91%	With potassium carbonate In propan-2-one for 4h; Reflux;
91%	Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate In propan-2-one at 20℃; for 0.25h; Stage #2: 3-bromo-1-propene In propan-2-one at 20℃; for 7.5h; Reflux;
90%	With potassium hydroxide; potassium iodide In ethanol for 24h; Heating;
87%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;
86.2%	With potassium carbonate In propan-2-one at 65℃; for 10h;
85%	With potassium carbonate In propan-2-one Reflux;	Procedure A: Synthesis of O-allylated substrates from phenols General procedure: The respective phenol (1 equiv) was added to a round bottom flask equipped with a stir bar and a refluxcondenser. This was followed by addition of acetone (0.2 M) to dissolve the phenol and addition of K2CO3(4 equiv) and allyl bromide (2 equiv) in a single portion. The reaction mixture was heated to reflux untilcompletion as monitored by TLC. After cooling to room temperature, ethyl acetate and H2O were addedto the reaction mixture to dissolve any precipitate, and the reaction mixture transferred to a separatingfunnel. The aqueous phase was extracted with ethyl acetate (3×). The combined organic phases weredried over MgSO4 and evaporated under reduced pressure to give the crude O-allylated substrate.Purification by column chromatography gave the product.
84%	With potassium carbonate In propan-2-one at 20℃; for 2h;
83%	With potassium carbonate In propan-2-one for 1h; Heating;
83%	With potassium carbonate In propan-2-one at 65℃;
82%	With potassium carbonate In propan-2-one at 50℃; for 6h;
80%	With potassium carbonate In propan-2-one for 6h; Reflux;
75%	With potassium carbonate In propan-2-one at 65℃; for 10h;	5.1.2 Synthesis of 4-(allyloxy)benzaldehyde (2) Allyl bromide (14.0mL, 163.7mmol) and K2CO3 (5.6g, 40.9mmol) were added into a solution of 4-hydroxybenzaldehyde (1) (10.0g, 81.9mmol) in dry acetone (40mL) and the mixture was stirred overnight at 65°C. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (30mL) and washed by water (30mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to give target benzaldehyde 2 (9.96g, 75%) as a colorless clear liquid.
75%	With potassium carbonate In propan-2-one at 65℃;	Synthesis of 4-(allyloxy)benzaldehyde(2) Allyl bromide (14.0 ml, 163.7 mmol)And anhydrous potassium carbonate (5.6 g, 40.9 mmol)Was added to a solution of 4-hydroxybenzaldehyde (1) (10.0 g, 81.9 mmol) in acetone (40 ml)The reaction solution was stirred and refluxed at 65 ° C overnight.After the completion of the reaction, the solvent acetone was distilled off under reduced pressure.The residue was dissolved in ethyl acetate (30 mL) and distilled water (30 mL) and extracted three times. The organic layer was dried over anhydrous magnesium sulfate,Ethyl acetate was distilled off under reduced pressure.The residue was subjected to silica gel column chromatography to obtain the intermediate benzaldehyde 2 (9.96 g, yield 75%, colorless liquid).
75%	With potassium carbonate In propan-2-one at 65℃;	1.a Step a: Synthesis of 4- (allyloxy) benzaldehyde (2): Allyl bromide (14.0 ml, 163.7 mmol) and anhydrous carbon(5.6 g, 40.9 mmol) was added to a solution of 4-hydroxybenzaldehyde (1) (10.0 g, 81.9 mmol) in acetone (40 ml)The reaction solution was stirred at 65 ° C overnight.After completion of the reaction, the solvent acetone was removed by distillation under reduced pressure.The residue was dissolved three times in ethyl acetate (30 mL) and distilled water (30 mL). The organic layer was dried over anhydrous magnesium sulfate and the ethyl acetate was distilled off under reduced pressure.The residue was purified by silica gel column chromatography to give the intermediate benzaldehyde 2 (9.96 g, 75%Colorless liquid).
74%	With potassium carbonate In propan-2-one Reflux;
74%	With potassium carbonate In propan-2-one at 20℃; for 19h; Inert atmosphere;
62%	With potassium carbonate In propan-2-one at 20℃; for 4h; Reflux;
	With ethanol; potassium carbonate
	With potassium hydroxide In ethanol
	With potassium carbonate In propan-2-one
	With potassium carbonate In propan-2-one Heating;
	With potassium carbonate In ethanol for 4h; Heating;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃;
	With potassium carbonate In propan-2-one at 60℃;
	Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate In propan-2-one for 0.5h; Heating; Stage #2: 3-bromo-1-propene In propan-2-one for 3.5h; Heating; Further stages.;
	Stage #1: 4-hydroxy-benzaldehyde With tetrabutylammonium bromide; sodium hydroxide In dichloromethane; lithium hydroxide monohydrate at 25 - 30℃; for 0.25h; Stage #2: 3-bromo-1-propene In dichloromethane; lithium hydroxide monohydrate at 20 - 30℃; for 8h;	2 Example 2: Preparation of(4-aUyloxy-benzylidene)-(4-fluoro-phenyl)-amine p-Hydroxy bezaldehyde (500.0g, 4.09mol) was added to a solution of sodium hydroxide (172g,4.30mol) in demineralized water (4.0L) and stirred. Dichloromethane (2.50L), terra butyl ammonium bromide (135.Og, 0.42 mol) were added to the above mixture and stirred at 25-300C for 15 minutes. Allyl bromide (400ml, 4.62 mol) was added and the reaction mass was stirred for 8 hours at 20-300C. The layers were separated; the aqueous layer was extracted with dichloromethane (1.0L). The combined organic layer was washed with a solution of sodium hydroxide (2x (15Og in 2.0L water)) and demineralized water (4.0 L). Organic layer was dried over sodium sulfate and concentrated at 40-500C. Isopropyl alcohol (500ml) was added to the reaction mass and distilled out under reduced pressure. Isopropyl alcohol (1.25L) was again added and the reaction mass was heated to 6O0C followed by addition of 4-fluoroaniline (465ml, 4.90 mol) and then the reaction mass was maintained for 2 hours at 60-650C. The reaction mixture was cooled at 0 to -1O0C, stirred for 2 hours, filtered and washed with n- hexane (1.0L) to afford 880g of the title compound having purity 96.55 % by HPLC.
	With potassium carbonate In propan-2-one Reflux;
	With potassium carbonate In propan-2-one
	With potassium carbonate
	With potassium carbonate In acetonitrile at 60℃;
	With potassium carbonate In propan-2-one at 20℃;	5.1.2 Synthesis of O-allylated and O-prenylated benzaldehydes 7 General procedure: A solution of substituted 4-hydroxybenzaldehyde (6, 40.9mmol) in dry acetone (20mL) was added K2CO3 (9.73g, 70.1mmol) portionwise, followed by allyl bromide or 1-chloro-3-methylbut-2-ene (40.9mmol) at room temperature. After 1-5h, the reaction mixture was then filtered and the filtercake was washed with acetone (20mL). The filtrate was concentrated under reduced pressure and the residue was dissolved in EtOAc (50mL), the organic layer was then dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was further purified by chromatography to afford target benzaldehydes 7.
	With potassium carbonate In propan-2-one Reflux;	4.2.9. Procedure for the synthesis of chalcones 27-32 via 8b-13b(Table 3, Scheme 4) General procedure: To a 250 mL round bottom flask containing substituted hydroxybenzaldehyde (5a or 6a or 7a or 8a or 9a or 10a) (1.9 mmol)in dry acetone (20 mL), allyl bromide (2.0 mmol) and anhydrous K2CO3 (3.8 mmol) were added. The remaining procedure was similar to that described for 1b. Compound 8b-13b obtained, respectively after column chromatography over silica gel with hexane-ethyl acetate (9:1) was treated with 4-chloroacetophenone (3 mmol) in methanol (20 mL) and 10% aqueous NaOH (4 mmol). The remaining procedure was similar to as described above. The desired compound 27-32 obtained after recrystallization from MeOH and water was characterized by 1H & 13C NMR and HRMS data.
	With potassium carbonate In propan-2-one at 65℃; for 12h;	1 Preparation of 4-(Allyloxy)benzaldehyde (3a) [00118] To a solution of 4-hydroxybenzaldehyde 1a (500 mg, 4.09 mmol) in acetone (10 mL) was added 3-bromoprop- 1-ene 2 (0.53 mL, 6.14 mmol) followed by potassium carbonate (848 mg, 6.14 mmol). The reaction mixture was heated at 65 °C for 12 h whereupon TLC showed the completion of the reaction. The reaction mixture was cooled to room temperature, filtered and concentrated in vacuo resulting in a crude residue which was treated with water and extracted with dichloromethane (“DCM”). The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford 620 mg (93% yield) of the title compound 3a as a colourless oil. The crude compound was used in the next step without further purification. MS (ES+): mlz = 204.10 [M+ACNjt
	With potassium carbonate In propan-2-one at 65℃; for 18h;	Preparation of intermediate 2 Weigh 10g of p-hydroxybenzaldehyde (1) in the reaction flask, add an appropriate amount of acetone dissolved raw materials,10 g of potassium carbonate was added, and 14 ml of allyl bromide was gradually added under an oil bath. Finally, 10 g of potassium carbonate solid was slowly added, and the mixture was heated at 65 ° CThe reaction was stirred for 18 hours and monitored by TLC. After completion of the reaction, acetone was spun and the product was extracted with water / ethyl acetate to remove carbonic acidPotassium ethyl acetate layer, wet-packed column, petroleum ether: ethyl acetate = 10: 1 column, the colorless transparent rearrangement of raw materials intermediates2 (4-allyloxybenzaldehyde).
	With potassium carbonate In propan-2-one at 20℃; for 2h; Inert atmosphere;
	With potassium carbonate In propan-2-one at 20℃; Reflux;
	With potassium carbonate In propan-2-one for 8h; Reflux;
	With potassium carbonate In propan-2-one at 20℃; Reflux;	1 (1) (1) Synthesis of Functionalized Organic Light Emitting Compound 1 To a solution of 4-hydroxybenzaldehyde (4.0 grams (g), 32.7 mmol, 1.0 equivalent (equiv.)) in acetone (40 mL), K2CO3 (13.6 g, 3.0 equiv.) and allyl bromide (4.3 mL, 1.5 equiv.) were added. The reaction mixture was stirred at room temperature for 2 hours and further heated to reflux overnight. After cooling to room temperature, the solution was filtered, washed with acetone and concentrated in vacuo, which afford 4-(allyloxy)benzaldehyde.
	With potassium carbonate; potassium iodide In propan-2-one for 2h; Reflux;

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[12]Ren, Tianhua; Chen, Qin; Zhao, Changbo; Zheng, Qiang; Xie, Haibo; North, Michael [Green Chemistry, 2020, vol. 22, # 5, p. 1542 - 1547]
[13]Current Patent Assignee: GUIZHOU UNIVERSITY - CN110183328, 2019, A Location in patent: Paragraph 0079-0083
[14]Yang, Yan-Long; Zhou, Hui; Du, Gang; Feng, Ke-Na; Feng, Tao; Fu, Xiao-Li; Liu, Ji-Kai; Zeng, Ying [Angewandte Chemie - International Edition, 2016, vol. 55, # 18, p. 5463 - 5466][Angew. Chem., 2016, vol. 128, p. 5553 - 5556,4]
[15]Current Patent Assignee: UNIV SOUTH CHINA TECH - CN114349788, 2022, A Location in patent: Paragraph 0073-0074
[16]Eicher, Theophil; Ott, Markus; Speicher, Andreas [Synthesis, 1996, # 6, p. 755 - 762]
[17]Shin, Jung Ha; Seong, Eun Young; Mun, Hyeon Jin; Jang, Yu Jeong; Kang, Eun Joo [Organic Letters, 2018, vol. 20, # 18, p. 5872 - 5876]
[18]Kwesiga, George; Kelling, Alexandra; Kersting, Sebastian; Sperlich, Eric; Von Nickisch-Rosenegk, Markus; Schmidt, Bernd [Journal of Natural Products, 2020, vol. 83, # 11, p. 3445 - 3453]
[19]Kim, Hyun J.; Jackson, W. Roy [Tetrahedron Asymmetry, 1994, vol. 5, # 8, p. 1541 - 1548]
[20]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]
[21]Qiu, Chenyu; Hu, Yan; Wu, Ke; Yang, Ke; Wang, Nan; Ma, Yue; Zhu, Heping; Zhang, Yi; Zhou, Yunfang; Chen, Chao; Li, Shanshan; Fu, Lili; Zhang, Xiuhua; Liu, Zhiguo [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 24, p. 5971 - 5976]
[22]Kathe, Prasad M.; Berkefeld, Andreas; Fleischer, Ivana [Synlett, 2021, vol. 32, # 16, p. 1629 - 1632]
[23]Gaspar, Boris; Carreira, Erick M. [Angewandte Chemie - International Edition, 2007, vol. 46, # 24, p. 4519 - 4522]
[24]Sabitha, Gowravaram; Swapna; Satheesh Babu; Yadav [Tetrahedron Letters, 2005, vol. 46, # 36, p. 6145 - 6148]
[25]Lee, Jeong-Hwan; Kawatsuki, Nobuhiro [Molecular Crystals and Liquid Crystals, 2007, vol. 470, # 1, p. 19 - 29]
[26]Cheng, Xinjian; Duan, Lian; Liu, Kaiqi; Xiao, Li [Journal of Materials Chemistry C, 2021, vol. 9, # 14, p. 4877 - 4887]
[27]Lv, Tian; Wu, Jianbing; Kang, Fenghua; Wang, Tingting; Wan, Boheng; Lu, Jin-Jian; Zhang, Yihua; Huang, Zhangjian [Organic Letters, 2018, vol. 20, # 8, p. 2164 - 2167]
[28]Zhu, Heping; Xu, Tingting; Qiu, Chenyu; Wu, Beibei; Zhang, Yali; Chen, Lingfeng; Xia, Qinqin; Li, Chenglong; Zhou, Bin; Liu, Zhiguo; Liang, Guang [European Journal of Medicinal Chemistry, 2016, vol. 121, p. 181 - 193]
[29]Current Patent Assignee: WENZHOU MEDICAL UNIVERSITY - CN105541700, 2016, A Location in patent: Paragraph 0050; 0054
[30]Current Patent Assignee: WENZHOU MEDICAL UNIVERSITY - CN106214677, 2016, A Location in patent: Paragraph 0090; 0091
[31]Andersen, Thomas L.; Donslund, Aske S.; Neumann, Karoline T.; Skrydstrup, Troels [Angewandte Chemie - International Edition, 2018, vol. 57, # 3, p. 800 - 804][Angew. Chem., 2018, vol. 57, # 3, p. 800 - 804,5]
[32]Utsumi, Tatsuki; Noda, Kenta; Kawauchi, Daichi; Ueda, Hirofumi; Tokuyama, Hidetoshi [Advanced Synthesis and Catalysis, 2020, vol. 362, # 17, p. 3583 - 3588]
[33]Sánchez-Cantalejo, Fernando; Priest, Joshua D.; Davies, Paul W. [Chemistry - A European Journal, 2018, vol. 24, # 65, p. 17215 - 17219]
[34]Claisen; Eisleb [Justus Liebigs Annalen der Chemie, 1913, vol. 401, p. 44]
[35]Lu, Yong-Hong; Hsu, Chain-Shu; Wu, Shin-Tson [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 225, p. 1 - 14]
[36]Ito, Yukishige; Kanie, Osamu; Ogawa, Tomoya [Angewandte Chemie, 1996, vol. 108, # 21, p. 2691 - 2693] Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B. [Tetrahedron, 2005, vol. 61, # 32, p. 7746 - 7755]
[37]Shimizu, Hiroki; Ito, Yukishige; Kanie, Osamu; Ogawa, Tomoya [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 23, p. 2841 - 2846]
[38]Kiec-Kononowicz; Szymanska [Il Farmaco, 2003, vol. 57, # 11, p. 909 - 916]
[39]Murakami, Hiromi; Minami, Tatsuya; Ozawa, Fumiyuki [Journal of Organic Chemistry, 2004, vol. 69, # 13, p. 4482 - 4486]
[40]Van Otterlo, Willem A.L.; Ngidi, E. Lindani; Kuzvidza, Samuel; Morgans, Garreth L.; Moleele, Simon S.; De Koning, Charles B. [Tetrahedron, 2005, vol. 61, # 42, p. 9996 - 10006]
[41]Liang, Guang; Yang, Shulin; Jiang, Lijuan; Zhao, Yu; Shao, Lili; Xiao, Jian; Ye, Faqing; Li, Yueru; Li, Xiaokun [Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 2, p. 162 - 167] Liang, Guang; Li, Xiaokun; Chen, Li; Yang, Shulin; Wu, Xudong; Studer, Elaine; Gurley, Emily; Hylemon, Phillip B.; Ye, Faqing; Li, Yueru; Zhou, Huiping [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1525 - 1529]
[42]Current Patent Assignee: CHIDAMBARAM VENKATESWARAN SRIN; IND-SWIFT LABORATORIES LIMITED - WO2009/157019, 2009, A2 Location in patent: Page/Page column 19
[43]Location in patent: scheme or table Yi, Wei; Cao, Rihui; Chen, Zhiyong; Yu, Liang; Wen, Huan; Yan, Qin; Ma, Lin; Song, Huacan [Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 5, p. 752 - 754]
[44]Location in patent: body text Alam, Athar; Pal, Chinmay; Goyal, Manish; Kundu, Milan Kumar; Kumar, Rahul; Iqbal, Mohd Shameel; Dey, Sumanta; Bindu, Samik; Sarkar, Souvik; Pal, Uttam; Maiti, Nakul C.; Adhikari, Susanta; Bandyopadhyay, Uday [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 24, p. 7365 - 7373]
[45]Location in patent: scheme or table Chang, Meng-Yang; Lee, Nien-Chia [Synlett, 2012, vol. 23, # 6, p. 867 - 872]
[46]Location in patent: scheme or table Zhu, Wu Fu; Zhai, Xin; Li, Sai; Cao, Yun Yun; Gong, Ping; Liu, Ya Jing [Chinese Chemical Letters, 2012, vol. 23, # 6, p. 703 - 706]
[47]Liu, Zhiguo; Tang, Longguang; Zou, Peng; Zhang, Yali; Wang, Zhe; Fang, Qilu; Jiang, Lili; Chen, Gaozhi; Xu, Zheng; Zhang, Huajie; Liang, Guang [European Journal of Medicinal Chemistry, 2014, vol. 74, p. 671 - 682]
[48]Sharma, Nandini; Mohanakrishnan, Dinesh; Sharma, Upendra Kumar; Kumar, Rajesh; Richa; Sinha, Arun Kumar; Sahal, Dinkar [European Journal of Medicinal Chemistry, 2014, vol. 79, p. 350 - 368]
[49]Current Patent Assignee: UNIVERSITY OF MIAMI - WO2016/154255, 2016, A1 Location in patent: Paragraph 00118
[50]Current Patent Assignee: WENZHOU MEDICAL UNIVERSITY - CN106187967, 2016, A Location in patent: Paragraph 0013; 0022; 0023
[51]Liu, Haidong; Ge, Liang; Wang, Ding-Xing; Chen, Nan; Feng, Chao [Angewandte Chemie - International Edition, 2019, vol. 58, # 12, p. 3918 - 3922][Angew. Chem., 2019, vol. 131, # 12, p. 3958 - 3962,5]
[52]Huang, Binbin; Li, Yanan; Yang, Chao; Xia, Wujiong [Chemical Communications, 2019, vol. 55, # 47, p. 6731 - 6734]
[53]Alavi, Seyed Jamal; Seyedi, Seyed Mohammad; Saberi, Satar; Safdari, Hadi; Eshghi, Hossein; Sadeghian, Hamid [Drug Development Research, 2021, vol. 82, # 2, p. 259 - 266]
[54]Current Patent Assignee: DOW INC - US2020/317999, 2020, A1 Location in patent: Paragraph 0103
[55]Gaikwad, Sunil V.; Gaikwad, Milind V.; Lokhande, Pradeep D. [Journal of Heterocyclic Chemistry, 2021, vol. 58, # 7, p. 1408 - 1414]

2
[ 40663-68-1 ]
[ 123-08-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With aniline at 30℃; for 0.333333h;
98%	With ammonium formate In methanol for 0.5h; Heating;
96%	With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 20℃; for 4h; Inert atmosphere;

96%	With palladium diacetate; sodium hydride In N,N-dimethyl acetamide; mineral oil at 25℃; for 4h; Inert atmosphere;	13 Under nitrogen protection,Palladium acetate (0.018 mmol, 6 mol%)And sodium hydride (60% in oil, 0.51 mmol, 1.7 equiv)Suspended in DMA (1.0 mL),Stir at 25 ° C for 5 minutes.Add compound 12 (0.3 mmol)In DMA (0.5 mL) solution,Then react at 25 ° C for 4 hours,Add ice water to stop the reaction,Adjust the pH to 3.5 with dilute hydrochloric acid,Extracted with ethyl acetate,Combine the extracts,Dry with sodium sulfate,Rotary and steamed,Purified by column chromatography,The product 13 was obtained in a yield of 96%.
92%	With boron dimethyl-trifluoro sulphide In dichloromethane at 20℃; for 1.5h;
91%	With sodium acetate; nickel In N,N-dimethyl-formamide for 18h; Ambient temperature;
88%	With aminomethyl resin-supported N-propylbarbituric acid In tetrahydrofuran at 20℃;
83%	With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide at 30℃; for 24h; Schlenk technique;	8 Example 8 Take a 10ml dry Schlenk reaction tube.In this order, for example, 0.3 mmol of B2Pin20.01 mmol NiCl 2 (DME),0.02 mmol organic ligand L4,With 0.4 mmol of lithium t-butoxide, the double-row tube was operated three times;Inject DMA 2ml, water 50ul, 0.1mmol methanol and 0.2mmol raw material (I);It was then vigorously stirred at 30 ° C for 24 h.After the reaction was completed, the pH was adjusted to 2 by adding 1 M hydrochloric acid, and then 20 ml of water was added thereto, and extracted with 20 ml of ethyl acetate, and the organic phase was collected and washed with saturated brine.It is dried over anhydrous magnesium sulfate, concentrated, and then separated with a 200 mesh silica gel column.Thus, the product (II) was obtained in a yield of 83%.
83%	With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;	4.1. Representative General Procedure for Nickel-Catalyzed Deprotecting Reaction General procedure: In glovebox, B2pin2 (76.17 mg, 0.3 mmol, 1.5 equiv), NiCl2(DME) (2.20 mg, 0.01 mmol, 0.05 equiv),6,6-dimethyl-2,2-dipyridyl (3.68 mg, 0.02 mmol, 0.10 equiv), LiOtBu (32 mg, 0.4 mmol, 2.0 equiv), and protected phenol (if solid) (0.2 mmol) were added to an oven-dried tube. The reaction tube wasequipped with a magnetic stir bar and sealed with Teflon-lined cap, refilled the system with argonand performed two more evacuation-backfill cycles, protected phenol was added by syringe underargon flow (if liquid). DMA (2.00 mL), H2O (50 μL), MeOH (25 μL) were added to the tubesequentially. The reaction mixture turned dark and was stirred at 30 °C for 24 h. When the reactionwas finished, 10 mL aqueous HCl (0.1 M) was added to the mixture and extracted with CH2Cl2 (2 ×10 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The resulting residue was purifiedby silica gel flash chromatography to give the product.
17%	Stage #1: 4-(2-propenyloxy)benzaldehyde With C₁₂H₃₇NiP₄⁽¹⁺⁾*C₂F₆NO₄S₂^(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 15h; Glovebox; Schlenk technique; Reflux; Inert atmosphere;	Procedure C: Catalysis General procedure: Inside a glovebox, a flame-dried 15 mL Schlenk tube was charged with [Ni(PMe3)4H](SO2CF3)2N (1.6 mg,2.48 μmol, 1 mol-%), and dry THF was added (0.16 M, 1.5 mL) using a Schlenk line. The O-allyl ether(0.25 mmol, 1 equiv) was then added under argon counter-flow. The reaction mixture was allowed to stirat room temperature for 30 minutes. This was followed by addition of pTsOH·H2O (1 equiv) and thereaction mixture was then heated to reflux for the time specified. The reaction was quenched by additionof ethyl acetate and water followed by transfer to a separating funnel. The aqueous phase was extractedwith ethyl acetate (3 × 5 mL), and the combined organic phases were then dried over MgSO4 and dried byrotary evaporation to give the crude alcohol, which was finally purified by column chromatography onsilica gel.

Reference： [1]Murakami, Hiromi; Minami, Tatsuya; Ozawa, Fumiyuki [Journal of Organic Chemistry, 2004, vol. 69, # 13, p. 4482 - 4486]
[2]Ganguly, Nemai C.; Dutta, Sanjoy; Datta, Mrityunjoy [Tetrahedron Letters, 2006, vol. 47, # 32, p. 5807 - 5810]
[3]Mao, Yujian; Liu, Ye; Hu, Yanwei; Wang, Liang; Zhang, Shilei; Wang, Wei [ACS Catalysis, 2018, vol. 8, # 4, p. 3016 - 3020]
[4]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN108218672, 2018, A Location in patent: Paragraph 0036
[5]Konieczny, Marek T.; Maciejewski, Grzegorz; Konieczny, Wojciech [Synthesis, 2005, # 10, p. 1575 - 1577]
[6]Yasuhara, Akito; Kasano, Atsushi; Sakamoto, Takao [Journal of Organic Chemistry, 1999, vol. 64, # 11, p. 4211 - 4213]
[7]Tsukamoto, Hirokazu; Suzuki, Takamichi; Kondo, Yoshinori [Synlett, 2003, # 8, p. 1105 - 1108]
[8]Current Patent Assignee: CHANGSHU INSTITUTE OF TECHNOLOGY - CN110256205, 2019, A Location in patent: Paragraph 0141-0145
[9]Meng, Chenkai; Niu, Haolin; Ning, Juehan; Wu, Wengang; Yi, Jun [Molecules, 2020, vol. 25, # 3]
[10]Kathe, Prasad M.; Berkefeld, Andreas; Fleischer, Ivana [Synlett, 2021, vol. 32, # 16, p. 1629 - 1632]

3
[ 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]

4
[ 40663-68-1 ]
[ 124755-24-4 ]
[ 515834-87-4 ]

Reference： [1]Synlett,2003,p. 87 - 90

5
[ 1189-93-1 ]
[ 40663-68-1 ]
[ 134443-12-2 ]

Yield	Reaction Conditions	Operation in experiment
41%	In toluene; xylene at 20℃;

Reference： [1]Ono, Takashi; Fujii, Shunsuke; Nobori, Tadahito; Lehn, Jean-Marie [Chemical Communications, 2007, # 1, p. 46 - 48]

6
[ 4630-80-2 ]
[ 40663-68-1 ]
[ 784148-89-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate;	Preparation c-4 Methyl 1-[[4-(allyloxy)phenyl](hydroxy)methyl]cyclopentanecarboxylate To a solution of methyl cyclopentanoate (3.84 g, 30.0 mmol), in tetrahydrofuran (30 mL) at -78° C. was added a solution of lithium diisopropylamide (15.0 mL of a 2M in tetrahydrofuran, 30.0 mmol) dropwise. The mixture was stirred for 2 hours and then 4-allyloxy benzaldehyde (2.12 g, 13.1 mmol) was added. The mixture was allowed to warm to ambient temperature and stirred for 18 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride and dried (anhydrous magnesium sulfate), filtered and evaporated. The residue was purified by flash column chromatography (hexanes to 50percent ethyl acetate/hexanes) to yield the title compound as a colorless oil (3.67 g, 97percent). LRMS (m/z): 273 (M-OH)+.
97%		To a solution of methyl cyclopentanoate (3. 84 g, 30. 0 MMOL), in tetrahydrofuran (30 mL) at-78 °C was added a solution of lithium DIISOPROPYLAMIDE (15. 0 mL of a 2M in tetrahydrofuran, 30. 0 MMOL) dropwise. The mixture was stirred for 2 hours and then 4-allyloxy benzaldehyde (2. 12 G, 13. 1 MMOL) was added. The mixture was allowed to warm to ambient temperature and stirred for 18 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride and dried (anhydrous magnesium sulfate), filtered and evaporated. The residue was purified by flash column chromatography (hexanes to 50percent ethyl acetate/hexanes) to yield the title compound as a colorless oil (3. 67 g, 97percent). LRMS (m/z) : 273 (M-OH) +.

Reference： [1]Patent: US2005/187266,2005,A1
[2]Patent: WO2004/92145,2004,A1 .Location in patent: Page 96-97

7
[ 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]

8
[ 40663-68-1 ]
[ 10035-16-2 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 7746 - 7755

9
[ 123-08-0 ]
[ 109-64-8 ]
[ 40663-68-1 ]
[ 3722-80-3 ]
[ 17954-81-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate; In acetonitrile; at 20 - 60℃; for 3 - 4h;Industry scale;	The exemplary process of the invention is shown schematically in Figure 1.0 Step (a): 4-(3-Bromopropyloxy)benzaldehyde (Compound 1)A dry Belatech glass reactor (30L) was flushed with argon and charged with 4- hydroxybenzaldehyde (588g, 4.8MoIe), 1,3-dibromopropane (4.976kg, 24.6MoIe) and anhydrous acetonitrile (24L) under argon. Dried powdered 5 potassium carbonate (1.66kg, 12MoIe) was added in portions to the stirred solution. The suspension was stirred at 55-60C and monitored by gas chromatography and cooled (ice bath) to room temperature as soon as the 4- hydroxybenxaldehyde had been consumed (3-4hr). Solids were removed by filtration (2L Buechner funnel) and washed with dry acetonitrile (3 x 300 mL). ,0 The combined solvents were reduced in volume by rotary evaporation (bath temperature 400C) and then the excess of 1,3-dibromopropane was removed by <n="21"/>high, vacuum distillation (bath temperature 400C). Crude product was obtained as a bright yellow oil (1350g). The crude product was purified by column chromatography under argon using 10 kg silica gel, eluting with a mixture of heptane:ethyl acetate (75L; 9:1, by vol.) followed by a mixture of heptane: ethyl acetate (HL; 4:1, by vol.). After 5OL of the first eluant had been eluted, fractions (50OmL) of eluate were collected and their purities checked by TLC. The fractions containing pure product were combined and dried by rotary evaporation (bath temperature 4O0C) to yield pure product as a colourless oil. Yield: 90Og (3.7MoIe, 77%). TLC: Rf = 0.38 (A). GC: purity > 95 % (rt = 12.7min). 1H-NMR analysis: deltaH (300MHz5 CD3OD): 2.35 (quint, 3J Ilambdaetaz, 2H), 3.58 (t, 3J 7.4Hz, 2H), 4.18 (t, 3J 7.4Hz, 2H), 6.95, 7.85 (2 x d, 3J 8.5Hz; 4H), 9.85 (s, IH).Comments:Acetone and THF as reaction solvents were also investigated and found to give inferior outcomes to acetonitrile.It is important to secure highly pure product in this step. Product contaminated with the elimination product leads in the next step to the corresponding porphyrin by-product containing an unsaturated propene group.The product is air sensitive. Formation of the oxidation product (the carboxylic acid) was observed during workup. Due to the air sensitivity of the product, column chromatography should be carried out under an argon atmosphere and the bottles of the collected fractions should be kept closed.Two main by-products, an elimination product and a dimer, formed in the reaction. By TLC analysis, three compounds were observed: 4-allyloxy- benzaldehyde (Rf - 0.42), product (Rf = 0.38) and 4-[3-(4- fo?nylphenoxy)propyloxy]benzaldehyde (Rf= 0.20). <n="22"/>By GC analysis four compounds were detected: excess 1,3-dibromopropane (rt = 4.525min); elimination product (rt = 9.725min); product (rt = 12.858min) and the dimer (rt = 19.75min).

Reference： [1]Patent: WO2007/74340,2007,A1 .Location in patent: Page/Page column title page; 18-20; Sheet 1/2

10
[ 19158-51-1 ]
[ 40663-68-1 ]
[ 946082-46-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With phenylsilane In ethanol at 23℃; for 2.5h;

Reference： [1]Gaspar, Boris; Carreira, Erick M. [Angewandte Chemie - International Edition, 2007, vol. 46, # 24, p. 4519 - 4522]

11
[ 1809-20-7 ]
[ 40663-68-1 ]
[ 1428182-85-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate In neat (no solvent) at 20℃; for 0.1h; Green chemistry;	Typical experimental procedure General procedure: To a stirred mixture of an aromatic aldehyde (2 mmol) and dialkyl phosphite (2 mmol) was added potassium phosphate (5 mol %) and stirring continued. Upon completion of the reaction (TLC), methylene chloride (10 mL) was added. After stirring for five minutes, the catalyst was separated by centrifugation and organic extract was syringed out. Removal of solvent from the organic extract furnished respective α-hydroxy phosphonate. In case of aliphatic aldehydes (1n and 1o), after stirring the reaction mixture overnight, it was worked-up as described above and the residue obtained after removal of solvent from the organic extract was chromatographed over silica gel. Elution with hexane-ethyl acetate (8: 2, v/v) furnished pure α-hydroxy phosphonate.

Reference： [1]Kulkarni, Makarand A.; Lad, Uday P.; Desai, Uday V.; Mitragotri, Satish D.; Wadgaonkar, Prakash P. [Comptes Rendus Chimie, 2013, vol. 16, # 2, p. 148 - 152]

12
[ 40663-68-1 ]
[ 1668-54-8 ]
[ 1465740-08-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5968 - 5970

13
[ 99-20-7 ]
[ 40663-68-1 ]
4,6,4',6'-di-O-(4-allyloxybenzylidene)-α,α-D-trehalose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With Amberlyst 15 In N,N-dimethyl-formamide; benzene for 48h; Reflux;	2.2. Synthesis of 4,6,4',6'-di-O-(x-allyloxybenzylidene)-α,α-D-trehalose(2-; 3- or 4-AllTD) General procedure: Trehalose acetals were synthesized based on a method previouslydescribed for the synthesis of 4,6,4',6'-di-O-(4-allyloxybenzylidene)-α,α-D-trehalose with some modifications[40]. The acetalization reaction was carried out using a two-neckround-bottom flask equipped with a DeaneStark trap, thermometerand reflux condenser. 30 mL of anhydrous benzene, 3.2 mL of2-, 3- or 4-allyloxybenzaldehyde and 1.13 g of Amberlyst 15 wereadded to a solution of 2.7 g (7.9 mmol) of dried trehalose in 15 mL of anhydrous DMF. The reaction was carried under reflux for 48 h.After this time, the catalyst was filtered off and benzene wasremoved under reduced pressure. A solution of the product in N,N-dimethylformamide(DMF) was treated several times with aqueous NaHCO3 and deionized water. The precipitate was washed threetimes with diethyl ether (30 mL) in order to remove x-allyloxybenzaldehyde.White powder was dried under a vacuum for 24 h.

Reference： [1]Burek, Malgorzata; Czuba, Zenon P.; Waskiewicz, Sylwia [Polymer, 2014, vol. 55, # 25, p. 6460 - 6470]

14
[ 40663-68-1 ]
[ 366-84-7 ]
C₂₀H₂₃NO₃ [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 42713 - 42719

15
[ 6093-68-1 ]
[ 40663-68-1 ]
3-((4-(allyloxy)phenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-4-hydroxy-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With diethylamine In ethanol at 20℃; for 4h;	General procedure: To a well stirred solution of an aldehyde 9 (2 mmol) and 4-hydroxycoumarin (11,4 mmol) in ethanol (4 mL) was added diethylamine (20 mol%) and stirring was continued at ambient temperature. Upon completion of the reaction (TLC), theresultant solid was filtered, washed with water, dried, washed again with a hexane-chloroform mixture (9:1, v/v) and dried. The resultant bis-coumarins, 12, were found to be pure for all practical purposes.

Reference： [1]Kupwade, Ravindra V.; Pandit, Kapil S.; Desai, Uday V.; Kulkarni, Makarand A.; Wadgaonkar, Prakash P. [Research on Chemical Intermediates, 2016, vol. 42, # 7, p. 6313 - 6325]

16
[ 40663-68-1 ]
[ 3619-22-5 ]
4-methyl-benzoic acid (4-allyloxy-benzylidene)-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With acetic acid In ethanol Reflux;	Synthesis of benzoic acid (4-allyloxybenzylidene)-hydrazide (5a-e) General procedure: Benzaldehyde undergoes nucleophilicaddition reaction with aromatic hydrazides resultingin the formation of hydrazones. The completion ofreaction and the homogeneity of the synthesized compounds were checked by TlC. Further theproduct formed was washed with petroleum ether,dried, recrystallized and characterized by spectralanalysis.Ethanolic solution of 4-allyloxy benzaldehyde(10 m mol) was added to a 10 m mol of ethanolicsolution of benzohydrazides and the reaction mixturewas stirred for 30 minutes at room temperature inthe presence of glacial acetic acid as catalyst. Afterreuxing for 3-5 h the completion of the reaction wasmonitored by TlC. The reaction mixture was cooledand placed in refrigerator overnight. The resultingsolid was fltered and washed with petroleum etherand recrystallised with ethanol.

Reference： [1]Therese, S Kulandai; Geethamalika [Oriental Journal of Chemistry, 2017, vol. 33, # 1, p. 335 - 345]

17
[ 40663-68-1 ]
[ 90925-43-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2269 - 2279

18
[ 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]

19
[ 719-98-2 ]
[ 40663-68-1 ]
S-(trifluoromethyl) 4-(allyloxy)benzothioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With disodium hydrogenphosphate; tetrakis(tetrabutylammonium)decatungstate(VI); In acetonitrile; at 20.0℃; for 96.0h;Inert atmosphere; Sealed tube; Irradiation;	General procedure: To a 8 mL glass vial was added TBADT (54.4 mg, 0.016 mmol, 8 mol %), aldehydes (0.2 mmol, 1.0 equiv), 6a (148.3 mg, 0.6 mmol, 3.0 equiv), Na2HPO4 (42.6 mg, 0.3 mmol, 1.5 equiv) and 0.5mL of CH3CN. The reaction mixture was degassed by bubbling with Ar for 15 s with an outlet needle and the vial was sealed with PTFE cap. The mixture was then stirred rapidly and irradiated with a 390 nm Blue LED (approximately 2 cm away from the light source) at room temperature for 96 h. Purification of the crude product by flash chromatography on silica gelusing the indicated solvent system afforded the desired product.

Reference： [1]Chinese Chemical Letters,2021,vol. 32,p. 3027 - 3030

20
[ 1067-87-4 ]
[ 40663-68-1 ]
(E)-1-(allyloxy)-4-(buta-1,3-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: Diethyl allylphosphonate With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: 4-(2-propenyloxy)benzaldehyde In tetrahydrofuran at 0℃; for 16h; Inert atmosphere;

Reference： [1]Bhowmik, Amit; Fernandes, Rodney A.; Gorve, Dnyaneshwar A.; Kumar, Praveen [Organic Letters, 2022]

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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.
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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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.
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P411
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P413
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P422
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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
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P501	Dispose of contents/container to ...
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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. 40663-68-1 ] {[proInfo.proName]}

Quality Control of [ 40663-68-1 ]

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[ 40663-68-1 ] Synthesis Path-Upstream 1~3

[ 40663-68-1 ] Synthesis Path-Downstream 1~20

Precautionary Statements-General

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