Benzenemethanol, 4-cyclohexyl-α-methyl- synthesis
- Product Name:Benzenemethanol, 4-cyclohexyl-α-methyl-
- CAS Number:29030-52-2
- Molecular formula:C14H20O
- Molecular Weight:204.31
18594-05-3
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Yield:29030-52-2 95%
Reaction Conditions:
with methanol;sodium tetrahydroborate at 0 - 20; for 0.5 h;Inert atmosphere;
Steps:
93.1 Step 1. Preparation of (1R *) 1 -(4-cyclohexylphenyl)-ethanol
Under nitrogen atmosphere, at 0 °C, to a stirred solution of 1-(4-cyclohexylphenyl)- ethanone (0.30 g, 1.50 mmol) in dry MeOH (15 mL), NaBH4 (0.11 g, 3.00 mmol) was added inone portion. The resulting reaction mixture was stirred at r.t. for 30 mm, and then acetone (0.1mL) was added, followed by evaporation of the solvents. The residue was taken up in EtOAc (20 mL) and sequentially washed with sat. NH4C1 solution (20 mL) and sat. NaHCO3 solution (3 x 20 mL) and sat. NaC1 solution (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to dryness, affording the title compound (0.29 g, 95%), which was used in the nextstep without any further purification. ‘H NMR (DMSO-d6): ? 7.23 (d, 2H, J= 8.1 Hz), 7.14 (d,2H, J= 8.1 Hz), 5.01 (d, 1H, J= 4.2 Hz), 4.70-4.62 (m, 1H), 2.48-2.41 (m, 1H), 1.84-1.65 (m,5H), 1.46-1.32 (m, 4H), 1.29 (d, 3H, J= 6.5 Hz), 1.27-1.16 (m, 1H).
References:
WO2014/144836,2014,A2 Location in patent:Paragraph 0948; 0949
827-52-1
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