Ethanol → HCID 22908542, compound

HRID 1734392Notes

Reaction equation

HRID 1734392 reaction equation
[CH2:1]1[O:21][C:4]2([CH2:9][CH2:8][C:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[CH:6][CH2:5]2)[O:3][CH2:2]1.C(O)C.C(OCC)(=O)C>[H][H]>[CH2:2]1[O:3][C:4]2([CH2:5][CH2:6][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:18])([F:20])[F:19])=[CH:12][CH:11]=3)[CH2:8][CH2:9]2)[O:21][CH2:1]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 22908554HCID 22908554, compound

Product 1

HCID 22908542HCID 22908542, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A mixture of (4-trifluoromethoxyphenyl)cyclohexen-4-one ethyleneketal (43.3 g, 0.144 mol), ethanol (200 ml), ethyl acetate (50 ml) and Pa-C (2 g) was stirred at room temperature for 10 hours in hydrogen atmosphere (at that time, hydrogen (3.59 l) was consumed), filtering off the catalyst from the reaction solution, distilling off the solvent under reduced pressure, to obtain 4-(4-trifluoromethoxyphenyl) cyclohexanone ethyleneketal (43.5 g) (m.p. 41.2° C.), adding thereto formic acid (250 ml), heating the mixture under reflux for 2.5 hours, feeding the reaction substance into water, extracting with a mixed solvent of toluene (400 ml) with ethyl acetate (100 ml), twice washing the resulting organic layer with water, drying over anhydrous MgSO4, filtering off anhydrous MgSO4, distilling off the solvent under reduced pressure and subjecting the resulting residue to column chromatography (silica gel, eluent: toluene), to obtain 4-(4-trifluoromethoxyphenyl)cyclohexanone (20.7 g). Yield: 47%.

Workup

  1. customwas consumed),
  2. filtrationfiltering off the catalyst from the reaction solution
  3. distillationdistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-f706a3636a6a40eea2258628a8bbeb4c
Source dataset
uspto-grants-1996_07
Patent number
US05534187

Reaction notes

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