Sodium Hydroxide → 2-Methoxyimino-2-(3-hydroxyphenyl)acetic acid

HRID 1382079Notes

Reaction equation

HRID 1382079 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]>CO>[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54365989Methyl 2-methoxyimino-2-(3-hydroxyphenyl)acetate

Product 1

HCID 543905512-Methoxyimino-2-(3-hydroxyphenyl)acetic acidYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

An aqueous solution of 2N sodium hydroxide (8 ml.) was added with stirring at ambient temperature to a solution of methyl 2-methoxyimino-2-(3-hydroxyphenyl)acetate (anti isomer) (1.56 g.) in methanol (30 ml.). After stirring for 3 hours at the same temperature, methanol was distilled off. To the residue was added water and the mixture was washed with ether. The aqueous layer was adjusted to pH 1 with 10% hydrochloric acid, subjected to salting-out and extracted with ether. The extract was washed with a sodium chloride aqueous solution and dried over magnesium sulfate. Ether was distilled off to give crystals of 2-methoxyimino-2-(3-hydroxyphenyl)acetic acid (anti isomer) (1.07 g.). The crystals were recrystallized from a mixture of petroleum ether and ether to give crystals (0.7 g.), mp 99° to 101° C. (dec.).

Workup

  1. distillationwas distilled off
  2. additionTo the residue was added water
  3. washthe mixture was washed with ether
  4. extractionextracted with ether
  5. washThe extract was washed with a sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. distillationEther was distilled off

Sources & evidence

ORD record
ord-be1337f0e3f24ad997ae9621ec0a04a3
Source dataset
uspto-grants-1989_02
Patent number
US04804752

Reaction notes

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