Dimethylformamide → {4-[(1,5-Dimethylhexyl)oxy]butyl}-1,3-dioxolane

HRID 414895

Reaction equation

HRID 414895 reaction equation
[H-].[Na+].CN(C)[CH:5]=[O:6].[CH3:8][CH:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([OH:15])[CH3:14]>O>[CH3:14][CH:13]([O:15][CH2:8][CH2:9][CH2:10][CH2:11][CH:5]1[O:6][CH2:12][CH2:13][O:15]1)[CH2:12][CH2:11][CH2:10][CH:9]([CH3:16])[CH3:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 964762-Heptanol, 6-methyl-

Product 1

HCID 66623666{4-[(1,5-Dimethylhexyl)oxy]butyl}-1,3-dioxolaneYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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%).

Workup

  1. customfitted with thermocouple, magnetic stirrer, condenser
  2. extractionextracted with methyltert-butyl ether (2×100 mL)
  3. dry with materialthe combined organic phase dried over magnesium sulphate
  4. customthe solvent removed in vacuo
  5. customThe pale yellow oil was chromatographed over silica gel

Sources & evidence

ORD record
ord-96543556ab9b474d9c1a8f42a558083f
Source dataset
uspto-grants-2012_01
Patent number
US08088725B2

Linked notes

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