Hydrogen iodide → HCID 20513474, compound

HRID 1164102Notes

Reaction equation

HRID 1164102 reaction equation
C([C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[C:17]=1[O:30]C)([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:4]([O:6]CC)=[O:5])#N.I>C(O)(=O)C>[OH:30][C:17]1[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[CH:19][CH:20]=[CH:21][C:16]=1[CH:3]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 20513493HCID 20513493, compound

Product 1

HCID 20513474HCID 20513474, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]-n-nonanoate (6.7 g), hydriodic acid (58%, 10 ml) and acetic acid (30 ml) was refluxed under heating for 45 hours. The reaction mixture was concentrated under reduced pressure, and the residue 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 residue were added potassium hydroxide (5 g) and methanol (30 ml), and the mixture was refluxed under heating for an hour. After evaporation, the residue was dissolved in water, and the aqueous solution was washed with diethyl ether, acidified with conc. hydrochloric acid and then extracted with diethyl ether. The extract was washed with water, dried and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 90 g, benzene-ethyl acetate 1:1) to give 2-[2-hydroxy-3-(o-tolyloxy)phenyl]-n-nonanoic acid (4.3 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 45 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was poured into water
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with aqueous sodium hydrogen sulfite and water in turn
  7. customdried
  8. customevaporated under reduced pressure
  9. additionTo the residue were added potassium hydroxide (5 g) and methanol (30 ml)
  10. temperaturethe mixture was refluxed
  11. temperatureunder heating for an hour
  12. customAfter evaporation
  13. dissolutionthe residue was dissolved in water
  14. washthe aqueous solution was washed with diethyl ether
  15. extractionextracted with diethyl ether
  16. washThe extract was washed with water
  17. customdried
  18. customevaporated under reduced pressure
  19. customThe residue was purified by column chromatography (silica gel 90 g, benzene-ethyl acetate 1:1)

Sources & evidence

ORD record
ord-3fbb0af4c6bf4c9da39c518f53a18c88
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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