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

HRID 470026Notes

Reaction equation

HRID 470026 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-802262a02220453eb5b636d049d8158b
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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