Acetone → N-(3,5-dimethyl-2-hydroxybenzyl)acrylamide

HRID 247654

Reaction equation

HRID 247654 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([NH:12][C:13](=[O:16])[CH:14]=[CH2:15])O.CC(C)=O>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:1][C:2]1[C:3]([OH:9])=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH2:10][NH:12][C:13](=[O:16])[CH:14]=[CH2:15]

Participants

6

Reactant 3

HCID 180AcetoneHCID 77712,4-DimethylphenolHCID 13543N-Methylolacrylamide

Product 1

HCID 14008274N-(3,5-dimethyl-2-hydroxybenzyl)acrylamideYield 84.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A flask equipped with a condenser and a stirrer was charged with 122 g of 2,4-dimethylphenol, 101 g of N-methylolacrylamide, 1.80 g of p-toluenesulfonic acid and 100 ml of acetone, and the mixture was reacted at 60° C. for 60 minutes with stirring. The obtained reaction mixture was poured into excess water to separate an organic layer. The organic layer was dissolved in 200 ml of methylene chloride, which was washed with three 100 ml portions of water to give 174 g of N-(3,5-dimethyl-2-hydroxybenzyl)acrylamide.

Workup

  1. customA flask equipped with a condenser and a stirrer
  2. customthe mixture was reacted at 60° C. for 60 minutes
  3. customThe obtained reaction mixture
  4. customto separate an organic layer
  5. dissolutionThe organic layer was dissolved in 200 ml of methylene chloride
  6. washwhich was washed with three 100 ml portions of water

Sources & evidence

ORD record
ord-855147608f414415ae4a431787888b5b
Source dataset
uspto-grants-1987_11
Patent number
US04709062

Linked notes

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