bicyclo[3.3.1]non-6-ene-3-carboxylic acid synthesis

4synthesis methods

Product Name:bicyclo[3.3.1]non-6-ene-3-carboxylic acid
CAS Number:56820-19-0
Molecular formula:C10H14O2
Molecular Weight:166.22

65437-67-4 Synthesis

Tricyclo[3.3.1.13,7]decanone, 4-[(methylsulfonyl)oxy]-, [1R-(1α,3β,4aα,5α,7β)]- (9CI)

65437-67-4
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bicyclo[3.3.1]non-6-ene-3-carboxylic acid

56820-19-0
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Yield:56820-19-0 99%

Reaction Conditions:

with potassium hydroxide in ethanol;water at 110;

Steps:

89.2 Step 2. bicyclo [3.3.1] non-6-ene-3-carboxylic acid

To a solution of the product of step 1 above (62 g, 254 mmol) in EtOH (600 mL) and water (600 mL) was added KOH (43 g, 762 mmol). The mixture was heated to 110 overnight. After cooling to rt, the mixture was acidified with 1N HCl to pH 2. After removing the most ethanol in vacuo, the mixture was extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (500 mL), dried over anhydrous Na 2SO 4, filtered off, and concentrated in vacuo to give the title compound (42 g, 99% yield).

References:

WO2020/248972,2020,A1 Location in patent:Page/Page column 156-157

700-58-3 Synthesis