Citric Acid → HCID 14579796, compound

HRID 1607278Notes

Reaction equation

HRID 1607278 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][CH2:8][C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C(=O)C)[C:12]=3[C:13]=2[CH3:14])=[CH:5][CH:4]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:12]=3[C:13]=2[CH3:14])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 311Citric AcidHCID 14579795HCID 14579795, compound

Product 1

HCID 14579796HCID 14579796, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-(p-methoxyphenethyl)-3-methyl-4-acetoxy-benzofuran (1 gm, 3 mmoles) in methanol (50 mL) and 1N sodium hydroxide (10 mL) was stirred at room temperature for a period of 10 minutes. The mixture was acidified with 20% citric acid and the volatiles were removed in vacuo. The aqueous residue was extracted with ether, washed with water, dried (Na2SO4), filtered, and concentrated to yield a residue that was chromatographed on silica gel. Elution with 15% ethylacetate in hexane yielded 2-(p-methoxyphenethyl)-3-methyl-4-hydroxybenzofuran, mp. 72°-75° C.

Workup

  1. customthe volatiles were removed in vacuo
  2. extractionThe aqueous residue was extracted with ether
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a residue that
  8. customwas chromatographed on silica gel
  9. washElution with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-fd00e92ae5134b5d9c89a619abe9f06e
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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