Acetic Anhydride → 3-Methyl-7-(o-tolylthio)-2,3-dihydrobenzofuran-2-one

HRID 1164114Notes

Reaction equation

HRID 1164114 reaction equation
O[C:2]1[C:7]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:16]([CH3:20])[C:17]([OH:19])=[O:18].C(OC(=O)C)(=O)C>>[CH3:20][CH:16]1[C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[C:2]=2[O:18][C:17]1=[O:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 131394282-[2-Hydroxy-3-(o-tolylthio)phenyl]propionic acid

Product 1

HCID 205134243-Methyl-7-(o-tolylthio)-2,3-dihydrobenzofuran-2-oneYield 74.7%

Procedure

A mixture of 2-[2-hydroxy-3-(o-tolylthio)phenyl]propionic acid (2.0 g) and acetic anhydride (5 ml) was refluxed under heating and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 30 g, benzene) to give 3-methyl-7-(o-tolylthio)-2,3-dihydrobenzofuran-2-one (1.4 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 30 g, benzene)

Sources & evidence

ORD record
ord-5fba9a8a67a54bcf9783b8989b6d6d1a
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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