P-Chloroacetophenone → Methyl (4-chlorobenzoyl)acetate

HRID 1605485Notes

Reaction equation

C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1.[CH3:14][O:15][C:16](=O)[O:17]C>>[CH3:14][O:15][C:16](=[O:17])[CH2:12][C:11](=[O:13])[C:8]1[CH:9]=[CH:10][C:5]([Cl:4])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 7467P-Chloroacetophenone

HCID 12021Dimethyl Carbonate

HCID 10942334Sodium Methoxide

Product 1

HCID 735885Methyl (4-chlorobenzoyl)acetate

Procedure

The procedure is as described in Example 1, except that 54 g of sodium methylate in 600 ml dimethylcarbonate are used and 154.5 g of p-chloro-acetophenone are added dropwise over a period of 2.5 hours at 60°C. Working up in accordance with Example 1 gives at 60°C 187 g (87% of the theoretical amount) of p-chloro-benzoylacetic acid methyl ester with a boiling point of 113°C/0.3 torr.

Sources & evidence

ORD record: ord-4c2f8f34708d46109956afaa5dfa603d
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03950381

Reaction notes

Loading…