반응 #5107

반응 방정식

4-p-t-butylphenoxy-1-butanol

nicotinic acid

thionyl chloride

→

Nicotinoyl chloride

용매

dichloromethane

반응 조건

후처리

1. 1
   온도at reflux for two hours
2. 2
   기타The excess thionyl chloride was removed in vacuo
3. 3
   세척After forty-eight hours the mixture was washed with one liter of saturated sodium bicarbonate
4. 4
   건조The dichloromethane solution was dried over magnesium sulfate
5. 5
   기타evaporated to a syrupy residue
6. 6
   기타The material was chromatographed on 1 kg of silica gel with elution by dichloromethane-methanol, 96:4

실험 절차

Nicotinoyl chloride was prepared by treating 100 g (0.81 mole) of nicotinic acid with 280 ml of thionyl chloride at reflux for two hours. The excess thionyl chloride was removed in vacuo and the crystalline acid chloride hydrochloride was suspended in 500 ml of dichloromethane. To the stirred mixture was added 66 g (0.30 mole) of 4-p-t-butylphenoxy-1-butanol dissolved in 400 ml of dichloromethane. After forty-eight hours the mixture was washed with one liter of saturated sodium bicarbonate. The dichloromethane solution was dried over magnesium sulfate and evaporated to a syrupy residue. The material was chromatographed on 1 kg of silica gel with elution by dichloromethane-methanol, 96:4, to afford 43.8 g (45%) of the nicotinate ester as an oil. The hydrobromide salt was prepared by treatment of a solution of 43.8 g in 800 ml of ethyl acetate with 30 ml of 4.5N hydrogen bromide in ether. The precipitate was collected, washed with pentane and dried, m.p. 132°-133° C.

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