Iodoethane → HCID 178440466, compound

HRID 653378Notes

Reaction equation

HRID 653378 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH3:6])[CH:2]1[C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.[CH2:20](I)[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:19][C:16]1[CH:15]=[CH:14][C:13]([C@H:10]2[CH2:11][CH2:12][C@H:7]([CH:2]3[O:1][CH:3]3[CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9]2)=[CH:18][CH:17]=1)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178440465HCID 178440465, compound

Product 1

HCID 178440466HCID 178440466, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.6 g of p-[trans-4-(1,2-epoxypentyl)cyclohexyl]phenol in 120 ml of acetone was treated with 1.89 ml of ethyl iodide and 3.24 g of powdered potassium carbonate while gassing with argon. The mixture was heated to reflux while stirring for 24 hours, then evaporated on a rotary evaporator and the residue was partitioned in diethyl ether/water. The aqueous phase was extracted three times with diethyl ether. The organic phases were washed twice with water, dried over magnesium sulphate, filtered and evaporated. Chromatographic separation of the resulting, yellowish oil (1.76 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95) gave 1.45 g (82%) of 4-ethoxy-1-[trans-4-(1,2-epoxypentyl)cyclohexyl]benzene as an oily liquid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customevaporated on a rotary evaporator
  4. customthe residue was partitioned in diethyl ether/water
  5. extractionThe aqueous phase was extracted three times with diethyl ether
  6. washThe organic phases were washed twice with water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customChromatographic separation of the resulting, yellowish oil (1.76 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95)

Sources & evidence

ORD record
ord-8f5aaecc63374cf4a44c46d45f944727
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Reaction notes

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