ChemicalBook CAS DataBase List 3-[4-(1,1-DiMethylheptyl)-2-(phenylMethoxy)phenyl]cyclohexanone

3-[4-(1,1-DiMethylheptyl)-2-(phenylMethoxy)phenyl]cyclohexanone synthesis

8synthesis methods

Product Name:3-[4-(1,1-DiMethylheptyl)-2-(phenylMethoxy)phenyl]cyclohexanone
CAS Number:70434-13-8
Molecular formula:C28H38O2
Molecular Weight:406.6

930-68-7
260 suppliers
$9.00/1g

70120-16-0 Synthesis

1-BroMo-4-(1,1-diMethylheptyl)-2-(phenylMethoxy)-benzene

70120-16-0
9 suppliers
$165.00/25mg

3-[4-(1,1-DiMethylheptyl)-2-(phenylMethoxy)phenyl]cyclohexanone

70434-13-8
10 suppliers
$725.00/10mg

Yield:-

Reaction Conditions:

with hydrogenchloride;copper(I) iodide in tetrahydrofuran;(2S)-N-methyl-1-phenylpropan-2-amine hydrate;

Steps:

1 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)-phenyl]cyclohexanone

EXAMPLE 1 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)-phenyl]cyclohexanone A solution of 75.0 g. (0.193 mol.) of 2-(3-benzyloxy-4-bromophenyl)-2-methyloctane in 200 ml. of tetrahydrofuran was slowly added to 9.25 g. (0.386 mol.) of 70-80 mesh magnesium metal. The resultant mixture was refluxed for 20 minutes and then cooled to -18° C. Cuprous iodide (1.84 g., 9.7 mmoles) was added and stirring was continued for 10 minutes. To the resultant mixture was slowly added a solution of 18.5 g. (0.193 mol.) of 2-cyclohexen-1-one in 40 ml. of tetrahydrofuran at such a rate that the reaction temperature was maintained below -3° C. with salt-ice cooling. The reaction mixture was stirred 30 minutes longer (t<0° C.) and then added to 500 ml. of 2N hydrochloric acid and 2 liters of ice water. The quenched reaction was extracted three times with 500 ml. portions of ether. The combined extract was washed twice with 100 ml. portions of water, twice with 100 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil was purified via column chromatography on 1.6 kg. of silica gel, eluted with 20% ether-cyclohexane to yield 62.5 g. (79.7%) of product as an oil. PMR: δ_CDCl₃^TMS 0.84 (m, terminal methyl), 1.27 (s, gem dimethyl), 3.32 (m, benzylic methine), 5.06 (s, benzylic methylene), 6.7-7.3 (m, ArH), and 7.32 (s, PhH). IR: (CHCl₃) 1709, 1613 and 1575 cm^-1. MS: m/e 406 (M⁺), 362, 321, 315and 91.

References:

US4306097,1981,A

70120-09-1 Synthesis