Acylation of Phenolic Group in 11,12-Dihydroglaziovine – DMAP as Catalyst

J.S. Bindra, and A.Grodski, J. Org. Chem., 42, 910, (1977)

  1. A solution of (+/-)-11,12-dihydroglaziovine (0.168 g, 0.56 mmol) in dichloromethane (10 mL) is stirred at ambient temperature under a nitrogen aŽosphere.  To this solution is added triethylamine (0.75 mL), DMAP (0.07 g), and acetic anhydride (0.05 mL).

  2. The reaction mixture is stirred for a further 30 min.

  3. To the solution is added dichloromethane (20 mL), and then the solution is washed with water (3 x 5 mL) followed by saturated sodium bicarbonate solution (1 x 5 mL).  The organic layer is dried (anhydrous magnesium sulfate), filtered, and concentrated to give a foam (0.234 g) which is crystallized from ether to afford (+/-)-1,O-acetyl-11,12-dihydroglaziovine (0.18 g, 95%, m.p. 176-178°C.

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Acylation

Acetylation

Phenol