Acetic Acid → HCID 20513444, compound

HRID 1164096Notes

Reaction equation

HRID 1164096 reaction equation
C([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:15]=1OC)([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:4]([O:6]CC)=[O:5])#N.I.C(O)(=O)C>O>[CH2:9]([CH:3]1[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[C:15]=2[O:5][C:4]1=[O:6])[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24841Hydrogen iodideHCID 20513412HCID 20513412, compound

Product 1

HCID 20513444HCID 20513444, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]-n-heptanoate (5.9 g), hydriodic acid (58%, 10 ml) and acetic acid (20 ml) was refluxed under heating for 48 hours. The reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with aqueous sodium hydrogen sulfite and water in turn, dried and evaporated under reduced pressure. To the oily residue was added acetic anhydride (5 ml), and the mixture was refluxed under heating for 10 minutes and then evaporated under reduced pressure. The resultant oily residue was purified by column chromatography (silica gel 80 g, benzene) to give oily 3-(n-pentyl)-7-(o-tolyloxy)-2,3-dihydrobenzofuran-2-one (2.5 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 48 hours
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with aqueous sodium hydrogen sulfite and water in turn
  5. customdried
  6. customevaporated under reduced pressure
  7. additionTo the oily residue was added acetic anhydride (5 ml)
  8. temperaturethe mixture was refluxed
  9. temperatureunder heating for 10 minutes
  10. customevaporated under reduced pressure
  11. customThe resultant oily residue was purified by column chromatography (silica gel 80 g, benzene)

Sources & evidence

ORD record
ord-bfd903581169431e897f4bc16aa040d5
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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