Citric Acid → 4-Hydroxy-2-(4-hydroxybenzyl)-3-methyl-5-propylbenzofuran

HRID 1607235Notes

Reaction equation

HRID 1607235 reaction equation
C(S)C.[H-].[Na+].[OH:6][C:7]1[C:12]2[C:13]([CH3:25])=[C:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)[O:15][C:11]=2[CH:10]=[CH:9][C:8]=1[CH2:26][CH2:27][CH3:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[OH:6][C:7]1[C:12]2[C:13]([CH3:25])=[C:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[O:15][C:11]=2[CH:10]=[CH:9][C:8]=1[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

Product 1

HCID 145797614-Hydroxy-2-(4-hydroxybenzyl)-3-methyl-5-propylbenzofuranYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under nitrogen atmosphere, ethanethiol (4.9 g; 80 mmoles) was added dropwise over 5 minutes to a mixture Of 99% sodium hydride (1.9 g; 80 mmoles) in dimethylformamide (100 ml). After stirring for 15 minutes, a solution of 4-hydroxy-2-(4-methoxybenzyl)-3-methyl-5-propylbenzofuran (2.4 g; 8mmoles) in dimethylformamide (5 ml) was added in one portion. The mixture was refluxed for 2 hours, cooled, acidified with 20% citric acid solution and extracted with ether. The ether solution was washed with water, dried (Na2SO4), filtered, concentrated, and chromatographed to obtain 2.2 g of the title compound as an oil which crystallized from an ether hexane mixture.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-09272324036d4d71821cc7bba82677c6
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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