Methyl iodide → 4-(4-Methoxyphenyl)cyclohexanone

HRID 1359460Notes

Reaction equation

HRID 1359460 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:15]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:15][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

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Product 1

HCID 109765814-(4-Methoxyphenyl)cyclohexanoneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

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 iodomethane (4.9 mL, 11.2 g, 78.6 mmol, 3 equiv.). The reaction was heated at 65° 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-methoxyphenyl)cyclohexanone (5.34 g, 100%). 1H NMR(CDCl3) 7.16 (dt, 2H), 6.87 (dt, 2H), 3.78 (s, 3H), 2.99 (tt, 1H), 2.47-2.53 (m, 4H), 2.20 (m, 2H) and 1.83-1.98 (m, 2H); MS (electrospray) m/e, 205 (M+1)+, Calcd for C13H16O2, 204.

Workup

  1. customAfter the solvent was removed
  2. additionthe residue was treated with H2O
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-0b914538b1ac4ac880ad1922f32f6734
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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