1-Hydroxycyclohexyl phenyl ketone → HCID 19070349, compound

HRID 1955494Notes

Reaction equation

HRID 1955494 reaction equation
[OH:1][C:2]1([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:16]([Si:18]([O:23][CH3:24])([O:21][CH3:22])[O:19][CH3:20])=[CH2:17]>C1(C)C=CC=CC=1>[OH:1][C:2]1([C:8](=[O:15])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:17][CH2:16][Si:18]([O:23][CH3:24])([O:21][CH3:22])[O:19][CH3:20])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 703551-Hydroxycyclohexyl phenyl ketoneHCID 76004Vinyltrimethoxysilane

Product 1

HCID 19070349HCID 19070349, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.4 g (70 mmol) of 1-hydroxy-1-benzoylcyclohexane, 11.75 ml (77 mmol) of vinyltrimethoxysilane and 1.28 g (1.4 mmol) of RuH2 (CO) (PPh3)3 in 100 ml of anhydrous toluene were stirred at reflux for 4.5 hours. Following concentration and chromatography (silica gel, CH2Cl2 /ethyl acetate), 12.2 g (49%) of a yellowish oil were obtained which was found to be pure by 1H-NMR spectroscopy but which was purified further by bulb-tube distillation (200° C., 0.2 mbar). 1H-NMR (CDCl3):1.01 ppm (2H, mc, Et-H2); 1.15-1.28 ppm (1H, m, cyclohexyl-H); 1.57-1.89 ppm (9H, m, cyclohexyl-H); 2.59 ppm (2H, mc, Et-H1); 3.33 ppm (1H, s, OH); 3.35 ppm (9H, s, Si(OCH3)3); 7.17-7.40 ppm (4H, M, Ph-H).

Workup

  1. temperatureat reflux for 4.5 hours
  2. concentrationconcentration and chromatography (silica gel, CH2Cl2 /ethyl acetate)

Sources & evidence

ORD record
ord-d2b3131fd3704010adc389b5e5d56c8e
Source dataset
uspto-grants-1998_07
Patent number
US05776658

Reaction notes

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