Methyl 4-Methylcyclohexanecarboxylate synthesis
- Product Name:Methyl 4-Methylcyclohexanecarboxylate
- CAS Number:51181-40-9
- Molecular formula:C9H16O2
- Molecular Weight:156.22
67-56-1
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Yield:51181-40-9 83%
Reaction Conditions:
with thionyl chloride in neat (no solvent) at 0 - 25; for 16 h;Inert atmosphere;Temperature;
Steps:
8 Synthesis of Methyl 4-methylcyclohexane-1-carboxylate (1):
To a solution of 4-methylcyclohexane-1-carboxylic acid (SM-1) (5 g, 35.1 mmol) in methanol (25 mL) was added thionyl chloride (5.1 mL, 70.3 mmol) at 0 °C under nitrogen atmosphere and then stirred for 16 h at room temperature. After consumption of the starting material (by TLC), volatiles were evaporated under reduced pressure. Crude mixture was diluted with EtOAc (20 mL) and washed with water (20 mL), saturated NaHCO3 solution (20 mL) and brine solution (20 mL). Separated organic layer was dried over Na2SO4 and concentrated to obtain compound 1 (4.5 g, 83%) as colorless liquid. (0383) 1H NMR: (400MHz, DMSO-d6): δ 3.57 (s, 3H), 2.24-2.18 (tt, J = 3.6, 12.2 Hz, 1H), 1.89-1.81 (m, 2H), 1.72-1.64 (m, 2H), 1.38-1.24 (m, 3H), 0.98-0.88 (m, 2H), 0.85 (d, J = 6.5 Hz, 3H). LCMS (m/z): 157.12 [M++1]
References:
WO2018/26763,2018,A1 Location in patent:Page/Page column 59
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