Methyl chloroformate → 4-Fluoro-2-methylphenyl Methoxyformate

HRID 450438Notes

Reaction equation

HRID 450438 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[OH-].[Na+].Cl[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:16][O:15][C:13](=[O:14])[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH3:9]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 1362954-Fluoro-2-methylphenol

Product 1

HCID 106790444-Fluoro-2-methylphenyl MethoxyformateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Fluoro-2-methyl-phenol (25 g, 0.2 mol) was added to a solution of sodium hydroxide (9.7 g, 0.24 mol) in water (160 mL) and the resultant solution was cooled to 0° C. Methyl chloroformate (24.2 g, 0.26 mol) was added dropwise at 0° C. At the completion of the reaction, the pH was adjusted to pH 8 with saturated aqueous Na2CO3 and then the mixture was extracted with ethyl acetate (3×300 mL). The combined organic extracts were washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to provide carbonic acid 4-fluoro-2-methyl-phenyl ester methyl ester (30 g, 82% yield). 1H NMR (300 MHz, DMSO-d6): δ 7.22-7.13 (m, 2H), 7.05 (m, 1H), 3.81 (s, 3H), 2.12 (s, 3H).

Workup

  1. customAt the completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate (3×300 mL)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b158359705647059b14b8863006dc2d
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

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