Hydrochloric Acid → 4-hydroxy-N-(3-hydroxypropyl)benzamide

HRID 2165420Notes

Reaction equation

HRID 2165420 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][OH:16].Cl>>[OH:16][CH2:15][CH2:14][CH2:13][NH:12][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7456MethylparabenHCID 90863-Amino-1-propanol

Product 1

HCID 133263004-hydroxy-N-(3-hydroxypropyl)benzamideYield 38.8%

Conditions

Temperature
120 °C

Procedure

A mixture of 76 g of methyl 4-hydroxybenzoate and 112.5 g of 3-amino-1-propanol was heated and stirred at 120° C. for 8 hours. The reaction mixture was acidified with 2N hydrochloric acid and then extracted with ethyl acetate and butanol. The combined extracts were concentrated in vacuo and the residue was recrystallized from acetonitrile to give 37.8 g of N-(3-hydroxypropyl)-4-hydroxybenzamide, m.p. 118°-120° C.

Workup

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate and butanol
  3. concentrationThe combined extracts were concentrated in vacuo
  4. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c51ce3f7203f44a893a0d07e9d4afc11
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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