Acetic Acid → HCID 136051898, compound

HRID 1388435Notes

Reaction equation

HRID 1388435 reaction equation
[N+:1](=[CH2:3])=[N-].[C:4](O)(=[O:6])C.[CH:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]([O:17][CH2:18]C)(=[O:16])C.CC[O:22]CC>>[CH3:4][O:6][N:1]=[C:3]([C:8]1[CH:13]=[CH:12][C:11]([OH:22])=[CH:10][CH:9]=1)[C:14]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 241BenzeneHCID 3283Diethyl Ether2×HCID 8857Ethyl AcetateHCID 9550Diazomethane

Product 1

HCID 136051898HCID 136051898, compound

Procedure

This material was dissolved in ether (50 ml.) and a solution of diazomethane in ether was gradually added thereto under ice-cooling until the color of the mixture was changed to yellow. Acetic acid was immediately added thereto and the mixture was washed with a sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. Ether was distilled off to give oily residue (8 g.). The oily residue was subjected to column chromatography on silica gel using a mixture of benzene and ethyl acetate (9:1) as developing solvent to give methyl 2-methoxyimino-2-(4-hydroxyphenyl)acetate (syn isomer) (6.39 g.).

Workup

  1. temperatureunder ice-cooling until the color of the mixture
  2. washthe mixture was washed with a sodium bicarbonate aqueous solution
  3. dry with materiala saturated sodium chloride aqueous solution and dried over magnesium sulfate
  4. distillationEther was distilled off
  5. customto give oily residue (8 g.)

Sources & evidence

ORD record
ord-01ecc7f6c2a143978ffea2c74339c3b3
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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