Hydrochloric Acid → HCID 136108965, compound

HRID 2412693Notes

Reaction equation

HRID 2412693 reaction equation
[OH-].[Na+].[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:7]([O:9]C)=[O:8].Cl>CO>[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 136051898HCID 136051898, compound

Product 1

HCID 136108965HCID 136108965, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 2N aqueous solution of sodium hydroxide (11 ml.) was added with stirring at ambient temperature to a solution of methyl 2-methoxyimino-2-(4-hydroxyphenyl)acetate (syn isomer) (2.1 g.) in methanol (30 ml.) and the mixture was stirred for 18 hours at ambient temperature. The reaction mixture was adjusted to pH 7 with 10% hydrochloric acid and methanol was removed. 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 ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. Ethyl acetate was distilled off to give crystals of 2-methoxyimino-2-(4-hydroxyphenyl)acetic acid (syn isomer) (1.5 g.).

Workup

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

Sources & evidence

ORD record
ord-a3cbde999c4647f59e9b533bb5c85bb2
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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