Methyl chloroformate → 4-Tert-butyl-2-chlorophenyl methyl carbonate

HRID 423815Notes

Reaction equation

HRID 423815 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([Cl:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:21]([O:23][CH3:24])=[O:22]>ClCCl.CN(C1C=CN=CC=1)C>[C:21](=[O:22])([O:23][CH3:24])[O:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][C:7]=1[Cl:12]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 73804-tert-Butyl-2-chlorophenolHCID 8471Triethylamine

Product 1

HCID 574702304-Tert-butyl-2-chlorophenyl methyl carbonateYield 93.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-tert-butyl-2-chlorophenol (47.0 g, 0.25 mol) in dichloromethane (200 mL) was added Et3N (50.5 g, 0.50 mol), DMAP (1 g) and methyl chloroformate (35.4 g, 0.38 mol) at 0° C. The reaction was allowed to warm to room temperature and stirred for additional 30 min. The reaction mixture was washed with H2O and the organic layer was dried over Na2SO4 and concentrated to give 4-tert-butyl-2-chlorophenyl methyl carbonate (56.6 g, 92%), which was used directly in the next step.

Workup

  1. washThe reaction mixture was washed with H2O
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d5e5afb634484463b2fe0704994a93ce
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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