Acetic Anhydride → 2-acetoxy-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-N-methylacetamide

HRID 617385Notes

Reaction equation

HRID 617385 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([OH:17])[C:13]([NH:15][CH3:16])=[O:14].[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1>[C:23]([O:17][CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][O:4][C:3]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:2]=1[CH3:1])[C:13]([NH:15][CH3:16])=[O:14])(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18357817Mandestrobin 2-Demethyl

Product 1

HCID 183577962-acetoxy-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-N-methylacetamideYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]-2-hydroxy-N-methylacetamide (0.57 g, 1.9 mmol) and acetic anhydride (0.43 g, 4.2 mmol) in pyridine (3 ml) was stirred at room temperature for 8 hours, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give the desired compound 2-acetoxy-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-N-methylacetamide (0.53 g, 82%) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-cee1a0ffd81c419193fe75f3eeafe9ae
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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