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

HRID 1723343Notes

Reaction equation

HRID 1723343 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-45a278753c7c4ca78439c2d337e73a23
Source dataset
uspto-grants-1989_08
Patent number
US04861791

Reaction notes

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