(+-)-2-Butanol → HCID 10219549, compound

HRID 1978247Notes

Reaction equation

HRID 1978247 reaction equation
[CH:1]([O:12][CH:13]([CH2:15][CH3:16])[CH3:14])(OC(CC)C)OC(CC)C.[C:17]1(=O)[CH2:22][CH2:21]C[CH2:19][CH2:18]1.CC(O)CC>[Fe](Cl)(Cl)Cl>[CH3:14][CH:13]([O:12][C:1]1[CH2:21][CH2:22][CH2:17][CH2:18][CH:19]=1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 7967CyclohexanoneHCID 5462422-[Di(sec-butoxy)methoxy]butane

Product 1

HCID 10219549HCID 10219549, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Conditions

Temperature
50 °C

Procedure

A mixture containing 116.2 g (0.5 mol) of tri(2-butyl) orthoformate, 49.10 g (0.5 mol) of cyclohexanone and 3.7 g (0.05 mol) of 2-butanol was stirred at room temperature (25° C.) and 0.2 g (1 mmol) of reagent grade iron (III) chloride was added. The temperature of the reaction mixture rose to about 35° C. due to the exotherm and was heated and maintained at about at 50° C. until gas-chromatographic analysis indicated that the reaction was complete. After removing the by-products 2-butyl formate and 2-butanol by distillation under reduced pressure, the resulting residue was subsequently distilled to provide 1-(2-butoxy)-1-cyclohexene (bp 86° C. @2 mm Hg) as a colorless liquid; the yield was 89.4% with a purity exceeding 99%.

Workup

  1. additionwas added
  2. customrose to about 35° C. due to the exotherm
  3. temperaturewas heated
  4. customAfter removing the by-products 2-butyl formate and 2-butanol
  5. distillationby distillation under reduced pressure
  6. distillationthe resulting residue was subsequently distilled

Sources & evidence

ORD record
ord-ee6f9031a9e44eea91850d49d6ec9849
Source dataset
uspto-grants-2001_05
Patent number
US06235944B1

Reaction notes

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