Citric Acid → HCID 14579765, compound

HRID 1607238Notes

Reaction equation

HRID 1607238 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; 4mmoles), potassium hydroxide pellets (1.5 g; 28mmoles), 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-c05b4acd346f4cb199dbf58af7dab81a
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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