Potassium Carbonate → Methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate

HRID 1504038Notes

Reaction equation

[N+](C1C=CC(C([O:10][CH:11]2[CH2:16][CH2:15][C:14]([C:18]([O:20][CH3:21])=[O:19])([CH3:17])[CH2:13][CH2:12]2)=O)=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:10][CH:11]1[CH2:12][CH2:13][C:14]([CH3:17])([C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 50 °C

Procedure

Into a 250-mL round-bottom flask containing a solution of 4-(methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoate (4.5 g, 14.00 mmol, 1.00 equiv) in methanol/water (30 mL/6 mL) was added potassium carbonate (5.8 g, 41.97 mmol, 3.00 equiv) and the resulting solution was stirred overnight at 50° C. The reaction was quenched by the addition of NH4Cl (aq.) and extracted with 3×100 mL of ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2) to afford the desired methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate (2.2 g, 91%) as a colorless oil.

Workup

customThe reaction was quenched by the addition of NH4Cl (aq.)
extractionextracted with 3×100 mL of ethyl acetate
washThe organic phase was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-c29feec15a87488c80859d20a87fc2fa
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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