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

HRID 1030675Notes

Reaction equation

HRID 1030675 reaction equation
C1(O[C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)C=CC=CC=1.[CH2:17]([CH2:19][NH2:20])[OH:18]>C(Cl)(Cl)Cl>[OH:18][CH2:17][CH2:19][NH:20][C:8](=[O:16])[C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 87250Phenylparaben

Product 1

HCID 156588N-(2-Hydroxyethyl)-4-hydroxybenzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 128.40g (.60 moles) of phenyl-4-hydroxybenzoate and 36.97g 606 moles) of ethanolamine was heated to 150° C. while stirring under a nitrogen atmosphere. After 2 hours at 150° C. the amber melt was cooled to ~150° C. and then poured into 1000 ml of chloroform. Within a few minutes a solid yellow precipitate formed. The precipitate was isolated by vacuum filtration washed with fresh chloroform and then air dried. This material was identified by NMR and IR spectroscopy as N-(2-hydroxyethyl)-p-hydroxybenzamide. A 95% yield was obtained.

Workup

  1. temperatureAfter 2 hours at 150° C. the amber melt was cooled to ~150° C.
  2. customWithin a few minutes a solid yellow precipitate formed
  3. customThe precipitate was isolated by vacuum filtration
  4. washwashed with fresh chloroform
  5. customair dried
  6. customA 95% yield was obtained

Sources & evidence

ORD record
ord-269a111c783d47f3a34db0a9f23a331a
Source dataset
uspto-grants-1992_04
Patent number
US05106921

Reaction notes

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