Hydrogen iodide → HCID 22390446, compound

HRID 1071929Notes

Reaction equation

HRID 1071929 reaction equation
I.[Cl:2][C:3]1[CH:8]=[C:7]([C:9]2(O)[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[OH:18]>C(O)(=O)C>[Cl:2][C:3]1[CH:8]=[C:7]([CH:9]2[CH2:10][CH2:11][C:12]([CH3:15])([CH3:16])[CH2:13][CH2:14]2)[CH:6]=[CH:5][C:4]=1[OH:18]

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 22390439HCID 22390439, compound

Product 1

HCID 22390446HCID 22390446, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

50 ml of an aqueous 57% hydriodic acid solution are added to 11.8 g of 2-chloro-4-(1-hydroxy-4,4-dimethylcyclohexyl)phenol in 200 ml of acetic acid. The reaction mixture is heated at reflux for 3 hours and the solvents are evaporated off under reduced pressure. Aqueous 40% sodium hydroxide solution, aqueous sodium carbonate solution and then aqueous sodium hydrogen sulphate solution are added and the resulting mixture is extracted with diethyl ether. The organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. The compound obtained is purified by chromatography on a column of silica gel, eluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hours
  3. customthe solvents are evaporated off under reduced pressure
  4. additionAqueous 40% sodium hydroxide solution, aqueous sodium carbonate solution and then aqueous sodium hydrogen sulphate solution are added
  5. extractionthe resulting mixture is extracted with diethyl ether
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. customthe solvents are evaporated off under reduced pressure
  8. customThe compound obtained
  9. customis purified by chromatography on a column of silica gel
  10. washeluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-13a9d4df732940c299b3208e90271238
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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