Ethanolamine → N-(2-Hydroxyethyl)-4-hydroxybenzamide

HRID 2165394Notes

Reaction equation

HRID 2165394 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][CH:3]=1.[CH2:12]([CH2:14][NH2:15])[OH:13]>CO>[OH:13][CH2:12][CH2:14][NH:15][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 7456Methylparaben

Product 1

HCID 156588N-(2-Hydroxyethyl)-4-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 80 g of methyl 4-hydroxybenzoate and 120 ml of ethanolamine was heated at 150° C. for five hours during which time 14.2 ml of methanol was distilled off. The excess ethanolamine was removed in vacuo, and the residue was treated with two 150 ml portions of chloroform. The chloroform was removed in vacuo and the residual oil dissolved in acetone from which the product crystallized to give 45.3 g of N-(2-hydroxyethyl)-4-hydroxybenzamide.

Workup

  1. distillationwas distilled off
  2. customThe excess ethanolamine was removed in vacuo
  3. additionthe residue was treated with two 150 ml portions of chloroform
  4. customThe chloroform was removed in vacuo
  5. dissolutionthe residual oil dissolved in acetone from which the product
  6. customcrystallized

Sources & evidence

ORD record
ord-d48b54dcac8946e39c89c2ed896696fa
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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