4-Chlorobenzoic Acid → Methyl 4-chlorobenzoate

HRID 867798Notes

Reaction equation

HRID 867798 reaction equation
[N+](=[CH2:3])=[N-].[Cl:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1>CCOCC>[Cl:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:3])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 63184-Chlorobenzoic AcidHCID 9550Diazomethane

Product 1

HCID 14307Methyl 4-chlorobenzoateYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An excess solution of diazomethane in ether was slowly added to an ice-cooled and stirred solution of p-chlorobenzoic acid (6.2 g, 39.6 mmol) in 50 ml of ether and the mixture was concentrated. The residue was recrystallized from 5 ml of MeOH to give a white crystalline product of methyl p-chlorobenzoate (4.8 g, 28.2 mmol, yield 71%). m.p. 42.0°-43.0° C. (recrystallized from methanol)

Workup

  1. temperaturecooled
  2. concentrationthe mixture was concentrated
  3. customThe residue was recrystallized from 5 ml of MeOH

Sources & evidence

ORD record
ord-2581470ef697489099656dc4bbc9e365
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

Loading…