Citric Acid → HCID 14579765, compound

HRID 1534203Notes

Reaction equation

HRID 1534203 reaction equation
[C:1]([C:9]1[O:10][C:11]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH3:21])=[C:15]([OH:22])[C:12]=2[C:13]=1[CH3:14])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].NN.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)CO>[CH2:1]([C:9]1[O:10][C:11]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH3:21])=[C:15]([OH:22])[C:12]=2[C:13]=1[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 13849539HCID 13849539, compound

Product 1

HCID 14579765HCID 14579765, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 2-benzoyl-4-hydroxy-3-methyl-5-propylbenzofuran (1.2 g; 4 mmoles), potassium hydroxide pellets (1.5 g; 28 mmoles), ethylene glycol (25 ml) and 99% hydrazine (0.7 ml) was heated at 135°-155° C. for 3 hours. The mixture was cooled, acidified with 20% citric acid solution, extracted with ether, dried (Na2SO4), filtered, concentrated, and chromatographed to obtain 650 mg of the title compound as an oil which was crystallized from hexane.

Workup

  1. temperaturewas heated at 135°-155° C. for 3 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ether
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-b89cf198fff54ef08454dde3b69041f1
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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