2-Chlorobenzoic Acid → Methyl 2-chlorobenzoate

HRID 867794

Reaction equation

HRID 867794 reaction equation
[N+](=[CH2:3])=[N-].[Cl:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]>CCOCC>[Cl:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:3])=[O:8]

Participants

4

Reactant 2

HCID 83742-Chlorobenzoic AcidHCID 9550Diazomethane

Product 1

HCID 11895Methyl 2-chlorobenzoateYield 72.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An excess solution of diazomethane in ether was added to an ice-cooled and stirred solution of o-chlorobenzoic acid (7.6 g, 48.6 mmol) in 50 ml of ether. After concentration, the residue was distilled under reduced pressure to give a colorless transparent oil of methyl o-chlorobenzoate (6.0 g, 35.2 mmol, yield 72.4%, b.p. 92°-93° C./7 mmHg), which was assigned the structure by the following data:

Workup

  1. temperaturecooled
  2. concentrationAfter concentration
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-3266c0d51b2249708da94ad3e0457107
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Linked notes

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