Hydroxyphenylacetic acid → 2-(4-Hydroxyphenyl)-N-methylacetamide

HRID 894334Notes

Reaction equation

HRID 894334 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1[C:17]([N+:18]([O-])=O)=CC=C(O)C=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH3:17][NH:18][C:9](=[O:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 9804-NitrophenolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 129230782-(4-Hydroxyphenyl)-N-methylacetamideYield 48.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 7.6 g of p-hydroxyphenylacetic acid in 100 ml of acetonitrile were added 8.4 g of p-nitrophenol and 10.3 g of dicyclohexylcarbodiimide at room temperature with stirring, and the resulting crystals of dicyclohexylurea were filtered out. An ethereal solution of 7.8 g of methylamine was added to the filtrate containing p-nitrophenyl p-hydroxyphenylacetate, the mixture was allowed to stand to precipitate crystals. The crystals obtained were filtered out and washed with diethyl ether to obtain 4.0 g of the title compound.

Workup

  1. filtrationthe resulting crystals of dicyclohexylurea were filtered out
  2. additionAn ethereal solution of 7.8 g of methylamine was added to the filtrate
  3. additioncontaining p-nitrophenyl p-hydroxyphenylacetate
  4. customto precipitate crystals
  5. customThe crystals obtained
  6. filtrationwere filtered out
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a876e0bd58734442ad69edd3678d3fd9
Source dataset
uspto-grants-1981_08
Patent number
US04283418

Reaction notes

Loading…