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

HRID 1905493Notes

Reaction equation

HRID 1905493 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-6e376a8ef4c447988d3b65d54bbda556
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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