(4-Chlorophenyl)acetic acid → Methyl 4-chlorophenylacetate

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.Cl.[CH3:13]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acid

HCID 21893726Hydrochloride methanol

Product 1

HCID 104196Methyl 4-chlorophenylacetate

Procedure

4-Chlorophenylacetic acid (5.0 g) was dissolved in 10% hydrogen chloride-methanol solution (50 ml) and heated under reflex for 14 hours. The solvent then was removed under reduced pressure and saturated sodium hydrogencarbonate solution was added to the residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and condensed under reduced pressure to provide methyl 2-(4-chlorophenyl)acetate (5.35 g) as a colorless, oily substance.

Workup

temperatureheated under reflex for 14 hours
customThe solvent then was removed under reduced pressure and saturated sodium hydrogencarbonate solution
additionwas added to the residue
extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate and condensed under reduced pressure

Sources & evidence

ORD record: ord-0989b2748d704d2894e860d20aea4ea4
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727998B2

Reaction notes

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