Methyl chloroformate → methyl N-(4-hydroxy-2-methylphenyl)carbamate

HRID 1597798Notes

Reaction equation

HRID 1597798 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[CH3:15].Cl[C:17]([O:19][CH3:20])=[O:18]>CC(C)=O>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:17](=[O:18])[O:19][CH3:20])=[C:9]([CH3:15])[CH:10]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 178194-Amino-m-cresol

Product 1

HCID 18932138methyl N-(4-hydroxy-2-methylphenyl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

12.0 g of potassium carbonate were added to a solution of 100 g of 4-amino-3-methylphenol in 400 ml of acetone cooled in an ice-water bath, followed by the addition of 80 ml of methyl chloroformate at the same temperature. The resulting mixture was stirred at the same temperature for 3 hours, at the end of which time the reaction mixture was filtered. The resulting filtrate was concentrated under reduced pressure to give 151 g (yield 100%) of the title compound as an amorphous powder.

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationwas filtered
  3. concentrationThe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-656dbfc0370b4e0598df5ac10a46b150
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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