Hydrochloric Acid → HCID 20360800, compound

HRID 596678Notes

Reaction equation

HRID 596678 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7].[CH3:16]O>>[OH:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:16])=[O:11])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2703964-(3-Hydroxyphenyl)-4-oxobutanoic acid

Product 1

HCID 20360800HCID 20360800, compound

Procedure

i. Hydrogen chloride was bubbled into a gently boiling solution of 3-(3-hydroxybenzoyl)propionic acid (40 g, 0.21 mole) in dry methanol (80 ml) until esterification was complete. The solution was poured into ice-water (700 ml) and the product extracted into ether. The combined ethereal solutions were washed in turn with water and sodium bicarbonate solution, dried, and finally evaporated under reduced pressure to give methyl 3-(3-hydroxybenzoyl)propionate (41g, 96 m.p. 101.5°-103° C). On recrystallisation from toluene, the pure ester had m.p. 102°-103.5° C.

Workup

  1. extractionthe product extracted into ether
  2. washThe combined ethereal solutions were washed in turn with water and sodium bicarbonate solution
  3. customdried
  4. customfinally evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e4e23439a834f818950c304211a9321
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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