Hydrochloric Acid → methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoate

HRID 2299743

Reaction equation

HRID 2299743 reaction equation
COC[O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][O:10][NH2:11])=[CH:7][CH:6]=1.O=[C:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C([O-])(=O)C.[Na+].Cl>C(OCC)(=O)C.CCCCCC.CO.C(O)(=O)C>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10]/[N:11]=[C:15](/[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)\[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 517045Sodium AcetateHCID 110522924-Methoxymethoxybenzyloxyamine

Product 1

HCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoateYield 50%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-methoxymethoxybenzyloxyamine (4.99 g), methyl 4-oxo-4-phenylbutyrate (5.71 g), acetic acid (5.10 ml), sodium acetate (4.87 g) and methanol (200 ml) was heated under reflux for 15 hours. The reaction mixture was cooled to room temperature, dilute hydrochloric acid was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (50 ml) and methanol (5 ml). To this solution was added 1N hydrochloric acid (10 ml) and heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-(4-hydroxybenzyloxyimino)-4-phenylbutyrate (4.24 g, yield 50%) as a colorless oil from an ethyl acetate-hexane (2:5, v/v)-eluted fraction.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  8. additionTo this solution was added 1N hydrochloric acid (10 ml)
  9. temperatureheated
  10. temperatureunder reflux for 3 hours
  11. temperatureThe reaction mixture was cooled to room temperature
  12. additionwater was added
  13. extractionextracted with ethyl acetate
  14. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  15. dry with materialdried (MgSO4)
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-bb5ca6f3f4ef4c96ab6478433d29b685
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Linked notes

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