Acetone → HCID 67179298, compound

HRID 1045062Notes

Reaction equation

HRID 1045062 reaction equation
CC(C)=O.Cl[C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[H][H].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>CO.CC(O)=O.C(Cl)Cl.O=[Pt]=O>[CH:9]1([CH:12]2[CH2:13][CH2:14][CH:15]([C:18]([CH3:19])=[O:20])[CH2:16][CH2:17]2)[CH2:8][CH2:7][CH2:6][CH2:11][CH2:10]1

Participants

8

Reactant 4

HCID 180AcetoneHCID 178418287HCID 178418287, compoundHCID 178418361HCID 178418361, compoundHCID 178468152HCID 178468152, compound

Product 1

HCID 67179298HCID 67179298, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolventHCID 10129899Acetic acid methanolSolvent

Procedure

The methylketone starting material for Example 60 in the table below was prepared from trans-4-(4-chlorophenyl)cyclohexyl-1-ethanone (1 g, 4.2 mmol) in two steps. Hydrogenation of the aromatic ring with concomitant reduction of the aromatic ketone to the alcohol and concomitant hydrogenolysis of the carbon-chlorine bond was accomplished using hydrogen gas (H2 pressure=50 psi) in a resealable glass pressure vessel equipped with a manometer and pressure valve. The reaction was stirred under H2 pressure for 2 days in MeOH:AcOH (1:1; 6 mL) using PtO2 (200 mg) as the catalyst to effect the desired transformation. Filtration through Celite® and evaporative workup gave the crude alcohol product (900 mg) which was used as-is in the preparation of the corresponding ketone by oxidation with PCC (6.3 mmol, 1.5 eq), the reaction being effected by stirring overnight in DCM containing molecular sieves (about 100 mg) at RT. The [4-(cyclohexyl)-cyclohexyl]methylketone product (700 mg) was isolated after workup and filtration through a silica gel column to remove impurities.

Workup

  1. customequipped with a manometer and pressure valve
  2. filtrationFiltration through Celite®
  3. customgave the crude alcohol product (900 mg) which

Sources & evidence

ORD record
ord-ea5951a81d5a4f4fa52dba701c899a6c
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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