Acetic Acid → HCID 13066703, compound

HRID 1164024Notes

Reaction equation

HRID 1164024 reaction equation
Cl.C[O:3][C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[CH:8][CH:7]=[CH:6][C:5]=1[C:18]([CH3:22])([CH3:21])[C:19]#N.C(O)(=[O:25])C>>[CH3:21][C:18]1([CH3:19])[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])[C:4]=2[O:3][C:22]1=[O:25]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 20513506HCID 20513506, compound

Product 1

HCID 13066703HCID 13066703, compound

Procedure

Conc. hydrochloric acid (20 ml) and acetic acid (60 ml) were added to 2-[2-methoxy-3-(o-tolyloxy)phenyl]-2,2-dimethylacetonitrile (5.7 g), and the mixture was refluxed under heating for 48 hours. After cooling, the reaction mixture was evaporated. Saturated aqueous solution of sodium bicarbonate (100 ml) was added to the oily residue and warmed. After cooling, the mixture was extracted with ethyl acetate, and the extract was washed with water, dried and evaporated. The solid residue was purified by recrystallization from a mixture of ethanol and n-hexane to give 3,3-dimethyl-7-(o-tolyloxy)-2,3-dihydrobenzofuran-2-one (2.5 g). mp 115°-117° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 48 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated
  5. additionSaturated aqueous solution of sodium bicarbonate (100 ml) was added to the oily residue
  6. temperaturewarmed
  7. temperatureAfter cooling
  8. extractionthe mixture was extracted with ethyl acetate
  9. washthe extract was washed with water
  10. customdried
  11. customevaporated
  12. customThe solid residue was purified by recrystallization from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-91428424a7454f299659428e710c336c
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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