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ChemicalBook CAS DataBase List 1,6-DIPHENYL-1,5-HEXADIENE-3,4-DIOL

1,6-DIPHENYL-1,5-HEXADIENE-3,4-DIOL synthesis

4synthesis methods
-

Yield:4403-20-7 67%

Reaction Conditions:

with triethylammonium formate;magnesium in methanol;water at 25; for 0.5 h;

Steps:

General procedure for the rapid pinacolization

General procedure: To a vigorously stirred suspension of triethylammonium formate (15 mmol), aromatic aldehyde/arylmethylketone (10 mmol) in aqueousmethanol (5 ml-) wasadded followed bymagnesium turnings (10 mmol). After thecompletion of the reaction, the reaction mixture was filtered and the residue was washed withwater, ethyl acetate (2 x 10 ml). The filtrate wasdiluted with water (25 ml) and repeatedly extractedwith ethyl acetate (3 x 15 ml). The combinedorganic extracts and washings were washed with water(2x 10 ml), dried over anhydrous sodium sulfate. Solvent removal under reduced pressure gave a white solid, which was further purified by recrystallization using dichloromethane andlight petroleum (40-60°C) to get pinacol as whitesolid.

References:

Pamar, M. Geeta;Govender;Muthusamy;Krause, Ruiw M.;Nanjundaswamy [Oriental Journal of Chemistry,2013,vol. 29,# 3,p. 969 - 974]

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