2-Methyl-2-butene → 4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

Participants

Reaction Steps

In a 2 liter three-necked round-bottomed flask, fitted with a mechanical stirrer, dropping funnel, and ground glass stopper, were charged 4-(6'-acryloyloxyhexyloxy)benzaldehyde (from Example 12) (22 grams; 0.1 mole), tertiary-butyl alcohol (500 mL), and 2-methyl-2-butene (available from Aldrich Chemical Co., Milwaukee, Wis.) (232 grams; 3 moles). The reaction mixture was stirred at room temperature. Over two hours, a solution of sodium chlorite (available from Aldrich Chemical Co., Milwaukee, Wis.) (65 grams; 0.7 mole) and sodium phosphate, monobasic monohydrate (available from Aldrich Chemical Co., Milwaukee, Wis.) (75 grams; 0.5 mole) in water (300 mL) was added. The reaction mixture was stirred for 12 hours at ambient temperature at which time the organic solvents were concentrated by rotary evaporator. The residue was then dissolved in diethyl ether (500 mL) and the mixture was made acidic (pH~2) by addition of 4N HCl. The mixture was poured into a separatory funnel and the organic layer was processed. The residue was recrystallized from ethanol. Spectral analysis confirmed the presence of 4-(6'-acryloyloxyhexyloxy)benzoic acid. The crystals weighed 15 grams which represents a 65 percent yield based on starting material.

Provenance & Evidence