Реакция #502080

Уравнение реакции

sodium hypochlorite

Dichloromethane

2-[(1,5-dimethylhexyl)oxy]ethanol

potassium bromide

→

oil

Выход 78.1%

[(1,5-dimethylhexyl)oxy]acetaldehyde

Выход 78.1%

Растворители

water

Условия реакции

Обработка

1. 1
   Другоеfitted with addition funnel, condenser
2. 2
   ЭкстракцияThe product was extracted with hexane (200 ml)
3. 3
   Промывкаwashed with water (2×200 ml)
4. 4
   СушкаThe organic phase was dried over sodium sulphate
5. 5
   Фильтрацияfiltered
6. 6
   Другоеthe solvent removed by evaporation

Методика

Dichloromethane (25 mL), 2-[(1,5-dimethylhexyl)oxy]ethanol (5 g, 29 mmol), a solution of potassium bromide (0.34 g, 2.9 mmol) in water (4.72 g) and 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO, 0.053 g, 0.34 mmol) was charged to 100 mL flask fitted with addition funnel, condenser, nitrogen, thermocouple and mechanical stirrer. A 2.8 wt % aqueous solution of sodium hypochlorite (173.5 g, 65 mmol) was added and the reaction stirred for a total of 15 hrs. The product was extracted with hexane (200 ml) and washed with water (2×200 ml). The organic phase was dried over sodium sulphate, filtered and the solvent removed by evaporation to yield a colourless oil (3.9 g). This oil (2 g) was chromatographed over silica gel (methyltert-butyl ether/hexane) to yield the product as a colourless oil (1.18 g, equating to a total chemical yield of 25%).

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