Sodium Hydroxide → (6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-acetic acid

Participants

Reaction Steps

(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-acetic acid ethyl ester (3.25 g, 14.6 mmol) was dissolved in absolute ethanol (50 ml). To this solution was added 1.0 N NaOH (20 ml). After stirring for 18 hours at ambient temperature, the reaction was then concentrated to 20 ml and partitioned between 0.1 N HCl and CH2Cl2. The CH2Cl2 layer was dried over MgSO4, filtered and concentrated under vacuum to give 2.79 g of the titled compound: C.I. m/z 195.1 [M+1]; 1H NMR (CDCl3)δ 4.78 (s, 1H), 4.77 (s, 1H), 3.02 (s, 1H), 2.75 (dd, J=4.9, 15.3 Hz, 1H), 2.56 (d, J=10.9 Hz, 1H), 2.49 (t, J=6.1 Hz, 1H), 2.38 (m, 1H), 2.24 (dt, 2.1, 12.0 Hz, 1H), 2.02 (m, 1H), 1.57 (dt, J=3.2,14.0 Hz, 1H), 1.26 (s, 3H), 1.19 (d, J=10.1,1H), 0.77 (s, 3H).

Provenance & Evidence