Chloroacetyl chloride → Benzenepropanoic acid, 4-(chloroacetyl)-, methyl ester

HRID 1153977Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-].C(OC(C)C)(C)C>ClCCl>[Cl:13][CH2:14][C:15]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:2][CH:3]=1)=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 50 g of methyl 3-phenylpropionate, 51.6 g of chloroacetyl chloride and 250 ml of dichloromethane was cooled to 0° C. Then at 0° to 10° C. with stirring, 122 g of aluminum chloride was added slowly, stirred at a room temperature for 2 hours and allowed to stand overnight. The reaction mixture was poured into an ice-concentrated hydrochloric acid and extracted with chloroform, then the chloroform layer was washed with water, dried and the chloroform was removed by distillation to obtain the residue, then isopropyl ether was added to the residue to effect crystallization. The crystals were collected by filtration, and recrystallized from ethanol to obtain 53.4 g of methyl 3-(4-chloroacetylphenyl)-propionate. Colorless needle-like crystals. Melting point: 90°-92° C.

Workup

stirringstirred at a room temperature for 2 hours
extractionextracted with chloroform
washthe chloroform layer was washed with water
customdried
customthe chloroform was removed by distillation
customto obtain the residue
customcrystallization
filtrationThe crystals were collected by filtration
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-62199e5afa814648bce5587d540a3508
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04487772

Reaction notes

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