Hydroxyphenylacetic acid → (2-Oxo-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)acetic acid

HRID 1193998Notes

Reaction equation

HRID 1193998 reaction equation
[C:1](O)(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)O.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1.S(=O)(=O)(O)O>>[O:10]=[C:1]1[CH:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:18]2[CH:17]=[C:16]([CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[CH:14][C:13]=2[O:12]1

Participants

4

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 1118Sulfuric AcidHCID 1292Mandelic Acid

Product 1

HCID 3059738(2-Oxo-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)acetic acidYield 88.5%

Procedure

75 g of mandelic acid and 75 g of 4-hydroxyphenylacetic acid are mixed in a round-bottomed flask. 800 ml of 80% strength sulfuric acid are added and the medium is then brought rapidly to 90° C. while being stirred. It is hydrolyzed with 2 kg of ice, the aqueous phase is extracted with 3 times 500 ml of ethyl acetate and the organic phase is washed with water, dried over anhydrous sodium sulfate and concentrated under vacuum. 117 g of a yellow oil are thereby obtained, which is purified by chromatography on 1200 g of silica (70-230 mesh), using a mixture of dichloromethane and methanol (98.5:1.5 v/v) as eluant. After evaporation of the solvent, the pure product is obtained.

Workup

  1. customis then brought rapidly to 90° C.
  2. extractionthe aqueous phase is extracted with 3 times 500 ml of ethyl acetate
  3. washthe organic phase is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-842291e61056413f8fdd9abd7fc374ae
Source dataset
uspto-grants-1989_03
Patent number
US04812469

Reaction notes

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