Methanol → Ethyl α-chlorobenzeneacetate

HRID 1842863Notes

Reaction equation

HRID 1842863 reaction equation
[Cl:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].C(N([CH2:17][CH3:18])CC)C.C[OH:20]>O>[Cl:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([O:20][CH2:17][CH3:18])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 102902Chloro(phenyl)acetyl chloride

Product 1

HCID 97752Ethyl α-chlorobenzeneacetateYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chlorophenyl acetyl chloride (53 mmol, 7.6 ml) was added dropwise to a solution of triethylamine (63.5 mmol, 8.7 ml) in methanol at 0° C. and the mixture was subsequently stirred for 3.5 h at room temperature. The reaction mix was then placed in 100 ml of water and repeatedly extracted with EtOAc (3×100 ml). Once combined, the organic phases were dried over MgSO4, concentrated under vacuum and 8.76 g (83.4%) of product was obtained.

Workup

  1. additionThe reaction mix
  2. extractionrepeatedly extracted with EtOAc (3×100 ml)
  3. dry with materialthe organic phases were dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4ca154e3fec744cbb44fa4f657c50d5d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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