Acetyl chloride → HCID 22713860, compound

HRID 352162Notes

Reaction equation

HRID 352162 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:14](Cl)(=O)C>CO>[N+:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:5]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 158763-Nitrophenylacetic acid

Product 1

HCID 22713860HCID 22713860, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of m-nitrophenylacetic acid, 14.2 g (78.0 mmol) in 200 mL of methanol at 0° C. was added 20 mL of acetyl chloride dropwise. The reaction mixture was stirred overnight at ambient temperature and concentrated to dryness. The residue was chromatographed on silica gel using 50% ethyl acetate/hexanes as eluent to yield 14.7 g (97%) of the desired mixture of isomers as a yellow oil. 1H—NMR is consistent with structure. MS (FD) 194.8 (M−1).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was chromatographed on silica gel using 50% ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-43c275d48b55462cb7c166f5af473336
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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