Ketone to Methylene

(Wolff-Kishner)

Examples:

Example 1

Alcohol to Ester reaction 6

A mixture of the SM (19.3 g, 75 mmoles) and hydrazine hydrate (18.8 g, 376 mmoles) was heated to 80 C. To the resulting suspension was added KOH (3.37 g, 51 mmoles) and the mixture was stirred at 80 C. Three additional portions of KOH (each 3.37 g, 51 mmoles) were added at 20 min intervals and the temp was raised to 110 C. After stirring overnight, the reaction mixture was acidified with cold portions of conc aq HCl. The product was extracted using MTBE (2 x 100 mL). The combined organics were washed with H2O (2 x 50 mL), brine (25 mL), and concentrated in vacuo until solids began to crystallize out of solution. The solids were filtered to provide the product. [US20080293730, page 8]