Potassium Hydroxide → HCID 68723612, compound

Participants

Reaction Steps

A solution of KOH (47.5 g, 0.72 mol) in EtOH (200 ml) was treated with methyl 7-methylspiro[4.5]dec-6-ene-6-carboxylate (15 g, 0.072 mol, prepared as described in Example 26) and the resulting mixture was stirred at reflux for 6 h, poured into cold 2N aqueous NaOH (300 ml), and extracted twice with cyclohexane (100 ml). The combined organic phases were washed with 2N aqueous NaOH (100 ml), and the combined aqueous phases were acidified with conc. HCl, and extracted twice with MTBE (150 ml). The combined organic phases were washed with water (100 ml), with a saturated aqueous solution of NaCl (150 ml), dried (MgSO4), and concentrated. FC (90 g SiO2, hexane/MTBE 88:12) of the crude product (12.8 g) gave 7-methylenespiro[4.5]decane-6-carboxylic acid (0.7 g, 5%) and 7-methylspiro[4.5]dec-7-ene-6-carboxylic acid (0.57 g, 4%).

Provenance & Evidence