Water → HCID 20566686, compound

Participants

Reaction Steps

Procedure B -- 2-t-Butylnitrobenzene (30.0 grams, 0.17 mole) in 100 milliliters of ether was added to a suspension of 8.22 grams (0.22 mole) of lithium aluminum hydride in 700 milliliters of ether at a temperature of 5°-10° C. The mixture was allowed to come to ambient temperature and stirred for an additional 0.5-hour period. Hydrolysis was accomplished by the successive addition of 15 milliliters of water, 15 milliliters of 20 percent aqueous sodium hydroxide, and 30 milliliters of water. After mixing for 2 hours, the inorganic salts were removed by filtration and the ether evaporated. The residue was applied to an activated neutral alumina column (200 grams, 80-200 mesh) and eluted with hexane at a flow rate of 10 drops per minute. The initial fractions (about 700 milliliters) were discarded and the product, a bright red band on the column, was collected. Evaporation of the hexane followed by crystallization of the residue from ethanol gave 4.6 grams (18.7 percent) of 2,2'-di-t-butylazobenzene melting point, 90°-91° C.

Provenance & Evidence