1-(2,3-Dichlorophenyl)ethanone

colorless to pale yellow liquid

Method A Method A α-Methyl-2, 3-dichlorobenzyl alcohol (5.0 g, 0.026 mol was dissolved in acetic acid (24 ml) and 12percent w/v sodium hypochlorite solution (23.26 ml, 0.0314 mol) was added slowly dropwise, with stirring, at a temperature of 15-25° C. α-Methyl-2, 3-dichlorobenzyl alcohol (5.0 g, 0.026 mol) was dissolved in acetic acid (24 ml) and 12percent w/v sodium hypochlorite solution (23.26 ml, 0.0314 mol) was added slowly dropwise, with stirring, at a temperature of 15-25° C. Under nitrogen, the 1-1- (2, 3-dichloro-phenyl) ethanol (7.00 g, 36.64 mmol) was dissolved in 80mL of dichloromethane, 10~35 ° C under a one-time addition of pyridinium chlorochromate (15.80 g, 73.28 mmol), stirred for 10~35 ° C for 3 hours, the mixture was trueConcentrated in vacuo and purified by column chromatography (offline wash: petroleum ether / ethyl acetate = 50 / 1~20 / 1) SeparationTo give 1- (2, 3-dichlorophenyl) ethanone (6.00 g, 86.62percent yield) as a yellow oil.The Grignard was added dropwise, with stirring, to acetyl chloride (301.91 g, 3.846 mol) dissolved in dry diethyl ether (1 liter) and anhydrous ferric chloride (1.925 g, 0.0118 mol) at a temperature of -70° C. under nitrogen. When addition was complete the resulting mixture was stirred at -70° C. for a further 5 minutes, and then allowed to come to room temperature. The reaction mixture was poured onto ice (5 liters) and stirred thoroughly. The aqueous mixture was basified with sodium carbonate and allowed to stand at room temperature overnight. The aqueous solution was extracted with diethyl ether (3*2 liters) and the ether phases combined, dried over anhydrous magnesium sulphate, filtered, and evaporated down. Crude The Grignard was added dropwise, with stirring, to acetyl chloride (301.91 g, 3.846 mol) dissolved in dry diethyl ether (1 liter) and anhydrous ferric chloride (1.925 g, 0.0118 mol) at a temperature of -70° C. under nitrogen. When addition was complete the resulting mixture was stirred at -70° C. for a further 5 minutes, and then allowed to come to room temperature. The reaction mixture was poured onto ice (5 liters) and stirred thoroughly. The aqueous mixture was basified with sodium carbonate and allowed to stand at room temperature overnight. The aqueous solution was extracted with diethyl ether (3*2 liters) and the ether phases combined, dried over anhydrous magnesium sulphate, filtered, and evaporated down. Crude 1- (2, 3-dichlorophenyl) ethanone (5.50 g, 29.09 mmol), Dimethylamine hydrochloride (9.49 g, 116.38 mmol), Paraformaldehyde (3.41 g, 37.82Mixed mmol) and concentrated hydrochloric acid lmL in 60mL of ethanol and heated to 80 ° C, stirring16 hours. The reaction solution was concentrated, diluted hydrochloric acid was added 20mL3N, washed with dichloromethane3 times, the aqueous phase was adjusted to pH 10 with 10percent aqueous potassium carbonate solution, ethyl acetate each time30mL and extracted 3 times with ethyl acetate phases combined, dried over anhydrous sodium sulfate, and concentrated in vacuoTo give 1- (2, 3-dichlorophenyl) -3- (dimethylamino) propan-1-one (2.40g, 33.52percentYield) as a yellow oil.

Molecular Weight:189.04
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:187.9795702
Monoisotopic Mass:187.9795702
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes