Citric Acid → HCID 14579779, compound

HRID 1534212Notes

Reaction equation

HRID 1534212 reaction equation
C(S)C.[H-].[Na+].C[O:7][C:8]1[CH:28]=[CH:27][C:11]([CH2:12][C:13]2[O:14][C:15]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][CH2:25][CH3:26])[C:16]=3[C:17]=2[CH3:18])=[CH:10][CH:9]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][C:13]2[O:14][C:15]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][CH2:25][CH3:26])[C:16]=3[C:17]=2[CH3:18])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 14579778HCID 14579778, compound

Product 1

HCID 14579779HCID 14579779, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under nitrogen, ethanethiol (3.1 gm; 50 mmoles) was added dropwise over 5 minutes to a mixture of 99% sodium hydride (1.2 gm; 50 mmoles) in dimethylformamide (100 mL). After stirring for 15 minutes, a solution of 2-(4-methoxybenzyl)-3-methyl-4-propyl-5-hydroxybenzofuran (2.1 gm; 6.7 mmoles) in dimethylformamide (DMF) (25 mL) was added in one portion. The mixture was refluxed for 1.5 hours, cooled, acidified with 20% citric acid and extracted with ether. The ether solution was washed with water, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting oil crystallised on standing at room temperature overnight. The crystals were slurried with hexane, filtered, washed with hexane, and air-dried to yield 2-(4-hydroxybenzyl)-3-methyl-4-propyl-5-hydroxybenzofuran, mp. 138°-142° C.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil crystallised
  9. waiton standing at room temperature overnight
  10. filtrationfiltered
  11. washwashed with hexane
  12. customair-dried

Sources & evidence

ORD record
ord-f0a689b3cf654fe5812bb77023aaccbf
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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