Phenolphthalein → HCID 136108965, compound

HRID 1388434Notes

Reaction equation

HRID 1388434 reaction equation
C1[CH:2]=[CH:3][C:4]2[C:10](C3C=CC(O)=CC=3)([C:11]3C=CC(O)=CC=3)[O:9][C:7](=[O:8])[C:5]=2C=1.[CH3:25][O:26][NH3+:27].[Cl-].C[O-].[Na+].Cl.[CH3:33][O:34]N>CO>[CH3:25][O:26][N:27]=[C:5]([C:4]1[CH:10]=[CH:11][C:33]([OH:34])=[CH:2][CH:3]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 4764PhenolphthaleinHCID 11639O-methylhydroxylammonium chlorideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 136108965HCID 136108965, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(a) Phenolphthalein indicator (3 drops) was added to a solution of 0-methylhydroxylamine hydrochloride (3.7 g.) in dry methanol (45 ml.). To the solution was dropwise added with stirring at ambient temperature 1 N methanol solution of sodium methoxide (39 ml.) until the color of the solution was changed to purplish red. O-Methylhydroxylamine hydrochloride was added thereto by small portions until the solution was changed to colorless solution. The mixture was stirred for 30 minutes at ambient temperature. After precipitating sodium chloride was filtered off, 2-(4-hydroxyphenyl)glyoxylic acid (6.56 g.) was added to the filtrate and the mixture was stirred for 1 hour at ambient temperature. After methanol was distilled off at low temperature, a saturated sodium chloride aqueous solution was added to the residue. The mixture was adjusted to pH 1 with 10% hydrochloric acid, subjected to salting-out and extracted with ether. The extract was dried over magnesium sulfate. Ether was distilled off at low temperature to give 2-methoxyimino-2-(4-hydroxyphenyl)acetic acid (syn isomer).

Workup

  1. additionTo the solution was dropwise added
  2. customAfter precipitating sodium chloride
  3. filtrationwas filtered off
  4. addition2-(4-hydroxyphenyl)glyoxylic acid (6.56 g.) was added to the filtrate
  5. stirringthe mixture was stirred for 1 hour at ambient temperature
  6. distillationAfter methanol was distilled off at low temperature
  7. additiona saturated sodium chloride aqueous solution was added to the residue
  8. extractionextracted with ether
  9. dry with materialThe extract was dried over magnesium sulfate
  10. distillationEther was distilled off at low temperature

Sources & evidence

ORD record
ord-7d48194d968d481597dd673a5fbf214e
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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