N-methyl-2-pyrrolidone → 2,3-Dimethylbenzoic acid

HRID 261722Notes

Reaction equation

HRID 261722 reaction equation
C(O[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH3:11])=O.Br([O-])(=O)=O.[K+].[C]=[O:18].CN1CCC[C:21]1=[O:25]>CCOC(CC(CC(OCC)=O)=O)=O.[Co]>[CH3:11][C:5]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]=1[C:21]([OH:25])=[O:18]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 19105568Formic acid, 2,3-dimethylphenyl ester2×HCID 23673461Potassium BromateHCID 178418416HCID 178418416, compound

Product 1

HCID 117822,3-Dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 131711489Diethyl acetone-dicarboxylate cobaltCatalyst

Procedure

A 100-ml. inner capacity stainless steel autoclave of a shaker type is charged with 22.5 grams (0.150 mol) of 2,3-xylyl formate. Further N-methyl pyrrolidone of 1.0 mol, a complex compound of diethyl acetone-dicarboxylate-cobalt of 0.036 mol and potassium bromate of 0.070 mol per mol of 2,3-xylyl formate, are added into the autoclave. Carbon monoxide is introduced into the autoclave under pressure, and the reaction is conducted at 270° C. for 2.0 hours, the maximum pressure being about 430 kg./cm.2 gauge. After termination of the reaction, the autoclave is cooled and the reaction product is taken away therefrom. The unreacted 2,3-xylyl formate is distilled off. Further distillation of the product liquor gives 9.60 grams (0.064 mol) of 2,3-dimethyl benzoic acid. This yield corresponds to a conversion of 42.7% based on the starting formic acid ester.

Workup

  1. customAfter termination of the reaction
  2. temperaturethe autoclave is cooled
  3. distillationThe unreacted 2,3-xylyl formate is distilled off
  4. distillationFurther distillation of the product liquor

Sources & evidence

ORD record
ord-40a2c062d2dd4c069b25dffd835e159d
Source dataset
uspto-grants-1979_05
Patent number
USRE029981

Reaction notes

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