3-Chlorobenzoic Acid → Methyl 3-chlorobenzoate

HRID 867796Notes

Reaction equation

HRID 867796 reaction equation
[N+](=[CH2:3])=[N-].[Cl:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9]>CCOCC>[Cl:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:3])=[O:9]

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 9550Diazomethane

Product 1

HCID 17946Methyl 3-chlorobenzoateYield 67.8%

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 m-chlorobenzoic acid (8.26 g, 52.8 mmol) in 50 ml of ether. The mixture was concentrated and distilled under reduced pressure to give a colorless transparent oil of methyl m-chlorobenzoate (6.1 g, 35.8 mmol, yield 67.8%, b.p. 116°-121° C./21 mmHg), which was assigned the structure by the following data:

Workup

  1. temperaturecooled
  2. concentrationThe mixture was concentrated
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-06bb9de62f11471b85bd9dabec40eb23
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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