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

HRID 1905520Notes

Reaction equation

HRID 1905520 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-9f33b64e65e44cffb070eb67da53c6f8
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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