Acetone → 4-(4-Benzyloxyphenyl)cyclohexanone

HRID 220156Notes

Reaction equation

HRID 220156 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.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CC(C)=O>O>[CH2:15]([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)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Product 1

HCID 212604934-(4-Benzyloxyphenyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(4-Hydroxyphenyl)cyclohexanone (4.98 g, 26.18 mmol), benzyl bromide (4.92 g, 28.79 mmol), K2CO3 (5.06 g, 36.65 mmol) and 75 mL of acetone were mixed in a reaction flask equipped with a reflux condenser. The mixture was heated to reflux and stirred overnight. The mixture was cooled to room temperature and water was added. The mixture was extracted with ethyl acetate three times. The combined organic layers were dried over Na2SO4, filtered and concentrated. The resulting solid was recrystallized in ethyl acetate to provide the titled compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.80-2.00 (m, 2 H), 2.13-2.26 (m, 2 H), 2.43-2.55 (m, 4 H), 2.91-3.05 (m, 1 H), 5.05 (s, 2 H), 6.94 (d, J=8.82 Hz, 2 H), 7.16 (d, J=8.82 Hz, 2 H), 7.28-7.48 (m, 5 H); MS (DCI) m/z 298 (M−NH4)+.

Workup

  1. customequipped with a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. extractionThe mixture was extracted with ethyl acetate three times
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting solid was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-567025c2b6aa425b85646d7b2c969efc
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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