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

HRID 544265Notes

Reaction equation

HRID 544265 reaction equation
CO[C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].[NH2:12][CH2:13][CH2:14][CH2:15][OH:16].Cl>>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])=[O:4])=[CH:6][CH:7]=1

Participants

4

Reactant 3

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

Product 1

HCID 133263004-hydroxy-N-(3-hydroxypropyl)benzamideYield 63.7%

Conditions

Temperature
120 °C

Procedure

Methyl p-hydroxybenzoate (11.5 g) was added to 17.0 g of 3-aminopropanol, and the mixture was stirred at 120° C. for 8 hours. Then, the reaction mixture was added to 1 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried. Evaporation of the solvent gave a crude product. The crude product was purified by silica gel column chromatography to give 9.3 g (yield 63.7%) of 4-hydroxy-N-(3-hydroxypropyl)benzamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. customdried
  4. customEvaporation of the solvent
  5. customgave a crude product
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b74a1dd00ad43ada7ca15136aacee0a
Source dataset
uspto-grants-1984_05
Patent number
US04448989

Reaction notes

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