Citric Acid → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

HRID 1534199Notes

Reaction equation

HRID 1534199 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:21])=[C:9]([C:11](=O)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:22][CH2:23][CH3:24].[OH-].[K+].NN.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(O)CO>[OH:1][C:2]1[C:7]2[C:8]([CH3:21])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 145797604-Hydroxy-2-(4-methoxybenzoyl)-3-methyl-5-propylbenzofuran

Product 1

HCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuranYield 58.6%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-hydroxy-2-(4-methoxybenzoyl)-3-methyl-5-propylbenzofuran (7.2 g; 22 mmoles), potassium hydroxide pellets (8.7 g; 155 mmoles), ethylene glycol (100 ml) and 99% hydrazine (3.0 ml) was heated with stirring and maintaining the internal temperature between 130° C. and 150° C. for 4 hours. The internal temperature was permitted to rise to 175° C. for 1 hour and excess water was always allowed to escape. The mixture was cooled and poured into excess 20% citric acid solution. The mixture was extracted with ether, washed with water, dried (Na2SO4), filtered, concentrated, and chromatographed to give 4 grams of the title compound.

Workup

  1. temperaturewas heated
  2. temperaturemaintaining the internal temperature between 130° C. and 150° C. for 4 hours
  3. temperatureThe mixture was cooled
  4. extractionThe mixture was extracted with ether
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed

Sources & evidence

ORD record
ord-d172ec0f45d946e38584b438c4f087b9
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

Loading…