Hydrochloric Acid → Ethyl 2-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butanoate

HRID 1584361Notes

Reaction equation

HRID 1584361 reaction equation
C([O:4][CH:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]CC2N=C(C3C=CC=CC=3)OC=2C)=[C:12]([O:30][CH3:31])[CH:11]=1)[C:6]#N)(=O)C.Cl.[O:33]1CCO[CH2:35][CH2:34]1.[OH2:39]>>[OH:4][CH:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:30][CH3:31])[CH:11]=1)[C:6]([O:33][CH2:34][CH3:35])=[O:39]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 212244242-Acetoxy-4-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]butyronitrile

Product 1

HCID 21224421Ethyl 2-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butanoateYield 60%

Procedure

A mixture of 2-acetoxy-4-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]butyronitrile (2.0 g), 6 N HCl (24 ml) and dioxane (12 ml) was stirred for 4 hours under reflux. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent. To the resulting oily product was added ethanolic hydrochloric acid (10%, 24 ml), followed by stirring for 1.5 hours under reflux. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), followed by distilling off the solvent. The resulting oily product was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:2, v/v), was obtained ethyl 2-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butanoate (0.73 g, 60%),

Workup

  1. temperatureunder reflux
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationby distilling off the solvent
  6. additionTo the resulting oily product was added ethanolic hydrochloric acid (10%, 24 ml)
  7. stirringby stirring for 1.5 hours
  8. temperatureunder reflux
  9. additionThe reaction mixture was poured into water, which
  10. extractionwas subjected to extraction with ethyl acetate
  11. washThe ethyl acetate layer was washed with water
  12. dry with materialdried (MgSO4)
  13. distillationby distilling off the solvent
  14. washFrom the fraction eluted with ethyl acetate-hexane (1:2

Sources & evidence

ORD record
ord-98a2914ddded40668da0be361a3fe5cc
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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