4-CARBOMETHOXY-CYCLOHEXANE-1-CARBOXYLIC ACID synthesis

Yield: 43%

Reaction Conditions:

with water;barium(II) hydroxide in methanol at 25; for 12 h;

Steps:

i.12.1 Step 1. Preparation of 4-(methoxycarbonyl)cyclohexanecarboxylic acid (i-12b).
Step 1. Preparation of 4-(methoxycarbonyl)cyclohexanecarboxylic acid (i-12b).A mixture of dimethyl cyclohexane-1,4-dicarboxylate (i-12a) (8 g, 40 mmol) and bariumhydroxide (6.3 g, 2Ommol) in 80% aqueous methanol (150 mL) was stirred at 25 °C for 12h.The mixture was diluted with water (200 mL) and washed with hexane (100 mLx2) to removeremaining starting material. The aqueous layer was then acidified with 2 M HC1 to pH = 3and extracted with EtOAc (100 mL x 3). The organic layer was washed with water (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The mixture was purified by column chromatography on silica gel (PE: EtOAc = 50:1 to 3:1) to afford the title compound (3.2 g, 43%) as a white solid. LCMS (ESI): calc’d for C9H1404 [M+H]: 187,found: 187;

References:

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