反应 #310852

反应方程式

isopropanol

8-bromo-6-octyn-1-ol

Jones reagent

→

8-bromo-6-octynoic acid

溶剂

sulphuric acid

water

diethyl ether

acetone

反应条件

后处理

1. 1
   其他prepared
2. 2
   洗涤washed with water
3. 3
   干燥a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
4. 4
   浓缩concentrated under reduced pressure

实验过程

To a solution of 2.1 g of 8-bromo-6-octyn-1-ol (prepared as described hereafter) in 20 ml of acetone was added dropwise 7.7 ml of a Jones reagent (prepared by dissolving 6.5 g of chromium trioxide in 5.75 ml of conc. sulphuric acid diluted with water to a volume of 25 ml) at 2° to 5° C. over a period of 40 minutes. To it was addded 3 ml of isopropanol. The reaction mixture was diluted with diethyl ether, washed with water, a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure to give crude 8-bromo-6-octynoic acid. The crude product, thus obtained, was dissolved in 20 ml of diethyl ether, and diazomethane-etherate was added with cooling in an ice bath until the solution was coloured pale yellow. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of benzene and ethyl acetate (50:1) as eluent to give 1.583 g of the title compound having the following physical characteristics:

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