Citric Acid → HCID 14579764, compound

HRID 1534202Notes

Reaction equation

HRID 1534202 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:7]=2[C:8]=1[CH3:9])(=O)[CH3:2].[OH-].[K+].NN.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)CO>[CH2:1]([C:4]1[O:5][C:6]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:7]=2[C:8]=1[CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 13849498HCID 13849498, compound

Product 1

HCID 14579764HCID 14579764, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-acetyl-4-hydroxy-3-methylbenzofuran (2 g; 10.5 mmoles), potassium hydroxide PG,72 pellets (4 g; 73 mmoles), ethylene glycol (50 ml) and 99% hydrazine (3 ml) was heated at 100° C. for 2 hours and at 180° C. for 2 hours. The mixture was acidified with excess 20% citric acid solution and extracted with ether. The ether layer was dried (Na2SO4), filtered, concentrated, and chromatographed to obtain 1.2 g of the title compound as an oil which crystallized from hexane.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-7db4bfc3d3484e92991f97402f4cf26c
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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