Hydrochloric Acid → Methyl 2-[2-(chloromethyl)phenyl]acetate

HRID 1419600Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]C(=O)O1.[CH3:12][O:13]C(Cl)Cl.[CH3:17][OH:18].[ClH:19]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[Cl:19][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[CH2:1][C:17]([O:13][CH3:12])=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1.0 g (6.75 mmol) of 3-isochromanone in 10 ml of toluene was added 2.68 ml (29.7 mmol) of dichloromethyl methyl ether, and the mixture was stirred at 60° C. for 24 hours. After cooling to room temperature, a mixed solution of 3 ml of methyl alcohol and 1.1 ml of pyridine was added thereto, followed by further stirring at room temperature for 24 hours. To the reaction mixture was added 20 ml of 1N hydrochloric acid, followed by extraction with 20 ml of ethyl ether. The combined ether extract was washed with two 20 ml portions of 1N hydrochloric acid. Ethyl ether was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 1.034 g (yield: 77.1%) of pure methyl 2-(chloromethyl)phenylacetate.

Workup

temperatureAfter cooling to room temperature
stirringby further stirring at room temperature for 24 hours
extractionfollowed by extraction with 20 ml of ethyl ether
extractionThe combined ether extract
washwas washed with two 20 ml portions of 1N hydrochloric acid
customEthyl ether was evaporated
customthe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record: ord-1f4ebcef532b4069a6c52d15c4f11876
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05886211

Reaction notes

Loading…