Sulfuric acid magnesium salt (1:1) → 2-Cyclohexenone, 5,5-dimethyl-

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Reaction Conditions

Reaction Steps

Dissolve 3-methoxy-5,5-dimethyl-cyclohex-2-enone (Tetrahedron 57 (2001) 217-225) (10.6 g, 68.7 mmol) in ether (500 ml) cool to 0° C., add dropwise a 1.5M solution of diisobutyl aluminum hydride (68.7 ml, 103 mmol), and stir for 30 minutes. Add saturated aqueous ammonium chloride (25 ml), stir 1 hour, add anhydrous magnesium sulfate (10 g), stir 1 hour. Filter through celite and concentrate. Dissolve the residue in ether (500 ml), add toluene-4-sulfonic acid monohydrate (650 mg, 3.44 mmol) and water (6.2 ml), and stir 1 hour. Wash with saturated aqueous sodium bicarbonate, brine, dry and concentrate to give the title compound as a clear oil (5.0 g, 58%): 1H NMR (CDCl3) δ 6.89-6.84 (m, 1H), 2.28 (s, 2H), 2.26-2.24 (q, 2H), 1.06 (s, 6H).

Provenance & Evidence