Benzene → 2-Methoxyimino-2-(3-hydroxyphenyl)acetic acid

HRID 1447244Notes

Reaction equation

HRID 1447244 reaction equation
[OH-].[Na+].[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1)[C:7]([O:9]C)=[O:8].Cl.C1C=CC=CC=1>O>[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54365989Methyl 2-methoxyimino-2-(3-hydroxyphenyl)acetate

Product 1

HCID 543905512-Methoxyimino-2-(3-hydroxyphenyl)acetic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2 N aqueous solution of sodium hydroxide (40 ml.) was added with stirring at ambient temperature to a suspension of methyl 2-methoxyimino-2-(3-hydroxyphenyl)acetate (syn isomer) (7.55 g.) in water (70 ml.) and the mixture was stirred for 1 hour at ambient temperature. The reaction mixture was adjusted to pH 6.5 with 10% hydrochloric acid, subjected to salting-out and washed with ether (60 ml.). The aqueous layer was adjusted to pH 1 with conc. hydrochloric acid and extracted once with 100 ml. of and twice with 60 ml. of ether. The extract was washed twice with a saturated sodium chloride aqueous solution (60 ml.) and dried over magnesium sulfate. Ether was distilled off to give oil. Benzene was added thereto and removed (twice) to give crystals of 2-methoxyimino-2-(3-hydroxyphenyl)acetic acid (syn isomer) (6.44 g.), mp 98° to 101° C. (dec.).

Workup

  1. washwashed with ether (60 ml.)
  2. extractionextracted once with 100 ml
  3. washThe extract was washed twice with a saturated sodium chloride aqueous solution (60 ml.)
  4. dry with materialdried over magnesium sulfate
  5. distillationEther was distilled off
  6. customto give oil
  7. customremoved (twice)

Sources & evidence

ORD record
ord-072c31bd7b8648bb9ae0565ee66b1b74
Source dataset
uspto-grants-1982_02
Patent number
US04316019

Reaction notes

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