Methyl chloroformate → 4-Fluoro-2-methylphenyl Methoxyformate

HRID 1384534Notes

Reaction equation

HRID 1384534 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 (100 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. 1H NMR Spectrum: (DMSOd6) 2.14(s, 3H); 3.81(s, 3H); 7.05(m, 1H); 7.1-7.25(m, 2H)

Workup

  1. extractionextracted with ethyl acetate (100 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-80c165434f894f1db381cf37501eed16
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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