Sulfuric Acid → 2-(2,3-Dihydro-2-oxo-3-phenyl-5-benzofuranyl)acetamide

HRID 476852Notes

Reaction equation

HRID 476852 reaction equation
S(=O)(=O)(O)O.[C:6](O)(=[O:15])[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)O.[OH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH2:27])=[O:26])=[CH:20][CH:19]=1>>[O:15]=[C:6]1[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:23]2[CH:22]=[C:21]([CH2:24][C:25]([NH2:27])=[O:26])[CH:20]=[CH:19][C:18]=2[O:17]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 1292Mandelic AcidHCID 86986(4-Hydroxyphenyl)acetamide

Product 1

HCID 142108072-(2,3-Dihydro-2-oxo-3-phenyl-5-benzofuranyl)acetamideYield 20%

Conditions

Temperature
80 °C

Procedure

190 ml of 80% strength sulfuric acid solution are added to a mixture of 16 g of mandelic acid and 15 g of 4-hydroxyphenylacetamide [J. Am. Chem. Soc. (1946) p. 2633]. The medium is heated very rapidly to 80° C. and immediately hydrolyzed using 600 g of ice. The aqueous phase is extracted with 3 times 200 ml of chloroform and the organic phase washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product obtained is recrystallized in chloroform.

Workup

  1. extractionThe aqueous phase is extracted with 3 times 200 ml of chloroform
  2. washthe organic phase washed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c4eb80ae7e4d4731beea4adb2b76daa4
Source dataset
uspto-grants-1989_12
Patent number
US04886799

Reaction notes

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