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

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. The mixture was stirred at 0° to 10° C. and 122 g of aluminum chloride was added gradually into the mixture. The reaction mixture was then stirred at a room temperature for 2 hours. The reaction mixture was allowed to stand overnight, then the reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid and was extracted with chloroform. The chloroform layer was washed with water, dried then chloroform was removed from the reaction mixture by distillation. The residue thus obtained was crystallized by adding isopropyl ether, and the crystals formed were collected by filtration, then recrystallized from ethanol to obtain 53.4 g of methyl 3-(4-chloroacetylphenyl)propionate in the form of needle-like crystals.

1. stirringThe reaction mixture was then stirred at a room temperature for 2 hours
2. additionthe reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid
3. extractionwas extracted with chloroform
4. washThe chloroform layer was washed with water
5. customdried
6. customchloroform was removed from the reaction mixture by distillation
7. customThe residue thus obtained
8. customwas crystallized
9. additionby adding isopropyl ether
10. customthe crystals formed
11. filtrationwere collected by filtration
12. customrecrystallized from ethanol

ORD record

ord-977a319933be4010a6d0839f07076ac0

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE034722