Benzyl Alcohol → 3-Benzyloxy-2-cyclohexen-1-one

HRID 1263511Notes

Reaction equation

HRID 1263511 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:9]([O:7][C:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[CH:2]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 104341,3-Cyclohexanedione

Product 1

HCID 108889653-Benzyloxy-2-cyclohexen-1-oneYield 96.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a round bottomed flask equipped with Dean-Stark apparatus was added 1,3-cyclohexanedione (60.0 g), toluene (450 ml), p-toluenesulfonic acid monohydrate (1.35 g) 30 and benzyl alcohol (52.6 g, 487). The resulting solution was heated to reflux temperature for 12 hr. The reaction mixture was cooled to room temperature and then washed with saturated aqueous sodium carbonate solution (2×100 ml). The organic layer was then washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated in vacuo, affording a brown oil (94.9 g) which crystallised upon standing for 17 hr. The crude crystalline material was slurried in isopropyl ether (20 ml). The mixture was filtered and the crystalline material was washed with ice cold isopropyl ether (3×30 ml), then with cold petroleum ether (2×20 ml). The resulting peach-colored crystalline solid was dried overnight under reduced pressure, furnishing the title compound (74.4 g, 76%). m/z (ES+) 203 (M+H+).

Workup

  1. customTo a round bottomed flask equipped with Dean-Stark apparatus
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux temperature for 12 hr
  4. washwashed with saturated aqueous sodium carbonate solution (2×100 ml)
  5. washThe organic layer was then washed with brine (100 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4b088365b3f4ca5a905203c6c19bdd2
Source dataset
uspto-grants-2003_04
Patent number
US06541473B2

Reaction notes

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