Dichloromethane → (2,6-Dichlorophenyl)methyl acetate

HRID 1692111

Reaction equation

HRID 1692111 reaction equation
ClCCl.[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:6]=1[CH2:7][OH:8].[C:14](OC(=O)C)(=[O:16])[CH3:15]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:6]=1[CH2:7][O:8][C:14](=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 27156Benzenemethanol, 2,6-dichloro-

Product 1

HCID 261530(2,6-Dichlorophenyl)methyl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent2×

Conditions

Temperature
5 °C

Procedure

Add 500 mL of dichloromethane to 100 g of 2,6-dichlorobenzyl alcohol followed by 117 mL of triethylamine. Cool the solution to 5° C. and add 65 mL of acetic anhydride. After 2.5 hr at room temperature, add another 10 mL of acetic anhydride, 20 mL of triethylamine and 0.5 g of 4-dimethylaminopyridine. Wash the organic layer with 1N HCl followed by saturated aqueous sodium bicarbonate and brine. Dry the organic layer (sodium sulfate) and evaporate to afford 131.5 g of the titled compound as an oil.

Workup

  1. washWash the organic layer with 1N HCl
  2. dry with materialDry the organic layer (sodium sulfate)
  3. customevaporate

Sources & evidence

ORD record
ord-459be403d19f41e198d4c744d78b0cf8
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Linked notes

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