Diazomethane → Methyl 3-(trifluoromethyl)benzoate

HRID 867793

Reaction equation

HRID 867793 reaction equation
[N+](=[CH2:3])=[N-].[F:4][C:5]([F:16])([F:15])[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10]>CCOCC>[F:4][C:5]([F:15])([F:16])[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH3:3])=[O:10]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 99633-(Trifluoromethyl)benzoic acid

Product 1

HCID 520213Methyl 3-(trifluoromethyl)benzoateYield 97.8%

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-trifluoromethylbenzoic acid (8.0 g, 42.1 mmol) in 50 ml of ether. After concentration, the residue was distilled under reduced pressure to give a colorless transparent oil of methyl m-trifluoromethylbenzoate (8.4 g, 41.2 mmol, yield 97.8%, b.p. 76°-78° C./12 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-d64fff4c7fa64ce4ab94f1133f1298f5
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Linked notes

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