2,2-Dimethoxypropane → 3-(4-Bromo-benzoyl)cyclohexanecarboxylic acid methyl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of trans-3-(4-bromobenzoyl)cyclohexane-1-carboxylic acid (500 mg, 1.61 mmol, obtained from Rieke Metals Inc., Lincoln, Nebr., USA) and 2,2-dimethoxypropane (669 mg, 6.43 mmol) in methanol (20 mL), 5 drops of 4 M HCl in dioxane was added, and this reaction mixture was heated at 50° C. overnight. The solvent was removed by rotary evaporation to give the product 3-(4-bromo-benzoyl)-cyclohexanecarboxylic acid methyl ester as a brown oil (500 mg, yield 95.7%). 1H NMR (300 MHz, DMSO) δ 7.80 (d, 2 H), 7.60 (d, 2 H), 3.70 (s, 3 H), 3.25 (m, 1 H), 2.50 (m, 1 H), 2.20–1.90 (m, 4 H), 1.70–1.50 (m, 4 H); LC-MS ret. time 3.30 min, m/z 324.9 (MH+).

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