Reaction #502077

Reaction equation

6-methylheptan-2-ol

Sodium hydride

dimethylformamide

→

2-{4-[(1,5-dimethylhexyl) oxy]butyl}-1,3-dioxolane

Yield 19.0%

Solvents

water

water

Conditions

Workup

1. 1
   Otherfitted with thermocouple, magnetic stirrer, condenser
2. 2
   Extractionextracted with methyltert-butyl ether (2×100 mL)
3. 3
   Dryingthe combined organic phase dried over magnesium sulphate
4. 4
   Otherthe solvent removed in vacuo
5. 5
   OtherThe pale yellow oil was chromatographed over silica gel

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.83 g, 20 mmol) and dimethylformamide (70 mL) were charged to a 250 mL three necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added dropwise over 10 minutes 6-methylheptan-2-ol (2.77 g, 21 mmol). The reaction mixture was stirred at room temperature for 90 minutes then water (10 mL) was added. The reaction mixture was poured into water (100 mL), extracted with methyltert-butyl ether (2×100 mL), the combined organic phase dried over magnesium sulphate and the solvent removed in vacuo. The pale yellow oil was chromatographed over silica gel to yield 2-{4-[(1,5-dimethylhexyl) oxy]butyl}-1,3-dioxolane as a colourless oil (1.4 g, 73% pure by GC RPA, 3.9 mmol, chemical yield 19%).

Source