Methyl 4-Methylcyclohexanecarboxylate synthesis

14synthesis methods

Product Name:Methyl 4-Methylcyclohexanecarboxylate
CAS Number:51181-40-9
Molecular formula:C9H16O2
Molecular Weight:156.22

67-56-1 Synthesis

67-56-1
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4331-54-8 Synthesis

4331-54-8
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51181-40-9
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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

120-61-6 Synthesis