Iodoethane → HCID 22145307, compound

HRID 1359461Notes

Reaction equation

HRID 1359461 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:22][CH3:23]>CC(C)=O>[CH2:22]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1)[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Product 1

HCID 22145307HCID 22145307, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-(4-hydroxyphenyl)cyclohexanone (5.0 g, 26.3 mmol) in acetone (100 mL) was treated with K2CO3 (14.5 g, 105 mmol, 4 equiv) and iodoethane (10.5 mL, 20.5 g, 131 mmol, 5 equiv.). The reaction was heated at 6520 C. overnight. After the solvent was removed, the residue was treated with H2O and extracted with EtOAc. The organic extracts were combined and washed with brine, dried over Na2SO4 and concentrated in vacuum to give the spectroscopically pure 4-(4-ethoxyphenyl)cyclohexanone (5.74 g, 100%). 1H NMR (CDCl3) 7.15 (dt, 2H), 6.86 (dt, 2H), 4.02 (q, 2H), 2.99 (tt, 1H), 2.46-2.54 (m, 4H), 2.16-2.24 (m, 2H), 1.83-2.00 (m, 2H) and 1.41 (t, 3H); MS (electrospray) m/e, 219 (M+1)+, Calcd for C14H18O2, 218.

Workup

  1. temperatureThe reaction was heated at 6520 C
  2. customovernight
  3. customAfter the solvent was removed
  4. additionthe residue was treated with H2O
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-46ea4010f1b04f438e6eb377f4c2c806
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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