1-Methanesulfonylcyclopropane-1-carboxylic acid synthesis

Yield:1249197-58-7 91%

Reaction Conditions:

Stage #1: 1-methanesulfonyl-cyclopropanecarboxylic acid ethyl esterwith methanol;sodium methylate at 0 - 20;
Stage #2:

Steps:

172.172-B

To a solution of ethyl 1-(methylsulfonyl)cyclopropanecarboxylate (0.95 g, 4.94 mmol) obtained in Example 172-A) in methanol (5 mL) was added a solution (28%, 0.60 mL, 5.44 mmol) of sodium methoxide in methanol at 0°C, and the mixture was stirred at room temperature for 30 min. A solution (28%, 1.2 mL, 10.88 mmol) of sodium methoxide in methanol was added, and the mixture was stirred for 2.5 hr. The mixture was neutralized with Dowex 50W-X8 (H⁺ form), the resin was filtered off, and washed with methanol. The filtrate was concentrated under reduced pressure to give the title compound (0.74 g) as a colorless solid (yield 91%). ¹H NMR (300 MHz, CDCl₃) δ 1.72-1.79 (2H, m), 1.85-1.94 (2H, m), 3.21 (3H, s). * The peak of "COOH group" was not observed.

References:

EP2530078,2012,A1 Location in patent:Page/Page column 144