Methyl chloroformate → 4-Fluoro-2-methylphenyl Methoxyformate

HRID 634659Notes

Reaction equation

HRID 634659 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH3:14])[CH:8]=1>[OH-].[Na+]>[C:2](=[O:3])([O:4][CH3:5])[O:13][C:10]1[CH:11]=[CH:12][C:7]([F:6])=[CH:8][C:9]=1[CH3:14]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 1362954-Fluoro-2-methylphenol

Product 1

HCID 106790444-Fluoro-2-methylphenyl MethoxyformateYield 78.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl chloroformate (6.8 ml, 88 mmol) was added over 30 minutes to a solution of 4-fluoro-2-methylphenol (10 g, 79 mmol) in 6% aqueous sodium hydroxide solution at 0° C. The mixture was stirred for 2 hours, then extracted with ethyl acetate (10 ml). The ethyl acetate extract was washed with water (100 ml) and dried (MgSO4) and the solvent removed by evaporation to give 4-fluoro-2-methylphenyl methyl carbonate (11.4 g, 78%) as an oil.

Workup

  1. extractionextracted with ethyl acetate (10 ml)
  2. extractionThe ethyl acetate extract
  3. washwas washed with water (100 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-375a1d14830b408e956998dd52a8e6f4
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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