Ethanol → HCID 68456339, compound

HRID 500529

Reaction equation

HRID 500529 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.C(O)C.[C:14]([OH:18])(=[O:17])[CH:15]=O>O>[C:3]1([CH3:2])[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][N:10]=[CH:15][C:14]([OH:18])=[O:17])[CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 760Glyoxylic AcidHCID 71562m-Tolylhydrazinium(1+) chloride

Product 1

HCID 68456339HCID 68456339, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
60 °C

Procedure

3-Methylphenylhydrazine hydrochloride (15.9 g, 100 mmol) was dissolved in water (450 mL) and ethanol (600 mL) with heating at 60° C. A solution of glyoxylic acid (9.21 g, 100 mmol) in water (100 mL) was added to the warm solution using water (3×15 mL) to rinse. The reaction mixture was stirred at 60° C. for 45 minutes and then cooled slightly and concentrated to remove ethanol. The aqueous mixture was neutralized with NaOH and then water was added (800 mL). The precipitate was filtered, washed with water (3×100 mL), washed with hexanes (100 mL) and dried to give the subtitle compound as a brown solid (12.2 g, 69%).

Workup

  1. washto rinse
  2. temperaturecooled slightly
  3. concentrationconcentrated
  4. customto remove ethanol
  5. additionwater was added (800 mL)
  6. filtrationThe precipitate was filtered
  7. washwashed with water (3×100 mL)
  8. washwashed with hexanes (100 mL)
  9. customdried

Sources & evidence

ORD record
ord-9a2a39e92d094dbda476973e38335bed
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Linked notes

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