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

HRID 12298

Reaction equation

HRID 12298 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

3

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 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

  1. temperatureheated under reflex for 14 hours
  2. customThe solvent then was removed under reduced pressure and saturated sodium hydrogencarbonate solution
  3. additionwas added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. 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
Patent number
US07727998B2

Linked notes

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