Hydrogen iodide → HCID 20513438, compound

HRID 1164093Notes

Reaction equation

HRID 1164093 reaction equation
C([C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[C:16]=1OC)([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:4]([O:6]CC)=[O:5])#N.I>C(O)(=O)C>[CH2:9]([CH:3]1[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[C:16]=2[O:5][C:4]1=[O:6])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 20513499HCID 20513499, compound

Product 1

HCID 20513438HCID 20513438, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]-n-octanoate (6.6 g), acetic acid (30 ml) and hydriodic acid (58%, 30 ml) was refluxed under heating for 48 hours. After cooling, acetic acid was distilled off under reduced pressure. To the residue was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, aqueous sodium hydrogen sulfite, aqueous sodium bicarbonate and water in turn, dried and then evaporated under reduced pressure. The oily residue (4.5 g) was subjected to column chromatography on silica gel (80 g) and eluted with benzene to give oily 3-(n-hexyl)-7-(o-tolyloxy)-2,3-dihydrobenzofuran-2-one (2.5 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 48 hours
  3. temperatureAfter cooling
  4. distillationacetic acid was distilled off under reduced pressure
  5. additionTo the residue was added water
  6. extractionthe mixture was extracted with diethyl ether
  7. washThe extract was washed with water, aqueous sodium hydrogen sulfite, aqueous sodium bicarbonate and water in turn
  8. customdried
  9. customevaporated under reduced pressure
  10. washeluted with benzene

Sources & evidence

ORD record
ord-66f95b78200c4b1db5ec2d3d38b35ca6
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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