Sodium Hydroxide → HCID 89650178, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 2-(2-allyl-6,6-dimethyl-cyclohexen-1-yl)acetate (1.5 g, 5.02 mmol) in dioxane (12 mL) and water (4 mL) was added NaOH (2M, 5.5 mL). The solution was heated to 100° C. for 30 h. The solution was concentrated in vacuo and water was added. The aqueous layer was extracted 2 times with ether and the organic layer was removed. Then, pH of the aqueous layer was adjusted to 1. The solution was extracted with ethyl acetate and washed with brine, dried and concentrated to give the desired product as a colourless oil (1.05 g, quant). 1H NMR (400 MHz, CDCl3) δ 5.77 (1H, dd, J=16.9, 10.3 Hz), 4.88-5.09 (2H, m), 3.13 (2H, s), 2.74 (2H, d, J=6.2 Hz), 1.96-2.08 (2H, m), 1.59-1.69, (2H, m), 1.43-1.57 (2H, m), 0.98-1.06 (6H, s) ppm.

Provenance & Evidence