Ethanol → HCID 22908542, compound

HRID 1378883Notes

Reaction equation

HRID 1378883 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 orgnaic 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-fe1c7ed70f804864b1846505aa37b2a4
Source dataset
uspto-grants-1997_09
Patent number
US05670085

Reaction notes

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