Water → alpha-Benzamido(2,3-dihydro-5-benzofuranyl)acetic acid

HRID 1390212Notes

Reaction equation

HRID 1390212 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.O[CH:11]([NH:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])[C:12]([OH:14])=[O:13].O>OS(O)(=O)=O.C(O)(=O)C>[C:16]([NH:15][CH:11]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)[C:12]([OH:14])=[O:13])(=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10329DihydrobenzofuranHCID 450272Alpha-Hydroxyhippuric acid

Product 1

HCID 23335824alpha-Benzamido(2,3-dihydro-5-benzofuranyl)acetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 23350293Acetic acid sulfuric acidSolvent

Procedure

2,3-Dihydrobenzofuran (4.8 g, 40 mmole) is stirred with 9.0 g (40 mmole) of α-hydroxyhippuric acid in 200 ml of 10% H2SO4 -acetic acid mixture. The reaction is run at room temperature for 0.5 hour. After the half-hour, the reaction mixture is poured into 500 ml of water. The aqueous solution is extracted with ethyl acetate (4 × 100 ml). The ethyl acetate extracts are dried over magnesium sulfate and then evaporated to give α-benzamido(2,3-dihydro-5-benzofuranyl)acetic acid. Recrystallization of the crude benzamido compound from hexane-methylene chloride gives 11.56 g (94% yield).

Workup

  1. extractionThe aqueous solution is extracted with ethyl acetate (4 × 100 ml)
  2. dry with materialThe ethyl acetate extracts are dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-41623b6da26643e2ba76adb546243291
Source dataset
uspto-grants-1979_02
Patent number
US04138397

Reaction notes

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