Advanced organic synthesis: methods and techniques by Richard S. Monson

By Richard S. Monson

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11 mole) of triphenylphosphine dissolved in 100 ml of acetonitrile is converted to triphenylphosphine dibromide. After the addition of the bromine has been completed, the cooling bath is removed, the flask is set up for vacuum distillation, and the solvent is removed. 08 mole), and the flask is heated at 200° (mantle, wax bath, or sand bath) until HBr ceases to be evolved (about 2 hours). -chlorobromobenzene in about 90% yield. Recrystallization from benzene gives the pure product, mp 65-66°. -methoxyphenol (59% yield).

05 mole) of 4-t-butylcyclohexanone in 160 ml of isopropanol in a 500-ml flask equipped with a reflux condenser. The solution is refluxed for 48 hours, then cooled, and the isopropanol is removed on a rotary evaporator. The residue is diluted with 65 ml of water and extracted four times with 40-ml portions of ether. The extracts are dried with anhydrous magnesium sulfate, filtered, and the ether is removed on the rotary evaporator. 5°. IV. Reduction of Conjugated Alkenes with Chromium (II) Sulfate Chromium (II) sulfate is capable of reducing a variety of functional groups under mild conditions (W).

The ether solution is washed with bicarbonate solution and water and dried over anhydrous sodium sulfate. Ether and unreacted oxide are removed on a rotary evaporator, and the product is recrystallized from petroleum ether, mp 82-83° (yield, 8 g). C. trans-4-BROMOCYCLOHEXANOL (18) HBr /\^ ^^OH " Br, To 10 g of cyclohexane-l,4-oxide is added 48% aqueous hydrobromic acid (60 g). The phases are mixed thoroughly and allowed to stand at room temperature until the solution separates into two layers (usually 5 days).

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