Water → 1-Isopropyl-3-oxocyclopentanecarboxylic acid

Reaction equation

[CH:1]([C:4]1([C:13]([O:15]C(C)(C)C)=[O:14])[CH2:8][CH2:7][C:6](OC)([O:9]C)[CH2:5]1)([CH3:3])[CH3:2].O>Cl.O1CCOCC1>[CH:1]([C:4]1([C:13]([OH:15])=[O:14])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([CH3:3])[CH3:2]

Participants

Procedure

tert-Butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate (8.32 g, 30.5 mmol) was dissolved in 4N anhydrous HCl in dioxane (50 mL) and water (10 mL) was added. The reaction mixture was stirred at rt overnight, then was concentrated. The residue was dissolved in DCM, dried over anhydrous MgSO4, filtered, and concentrated to give 1-isopropyl-3-oxocyclopentanecarboxylic acid (used without purification). 1H NMR (500 MHz, CDCl3) δ 2.70 (d, J=18.1 Hz, 1H), 2.44-2.39 (m, 1H), 2.30-2.15 (m, 2H), 2.14 (dd, J=18.1, 1.0 Hz, 1H), 2.06 (p, J=6.9 Hz, 1H), 1.98 (m, 1H), 0.98 (dd, J=11.4, 6.9 Hz, 6H).