Sulfuric Acid → 2-Oxabicyclo[2.2.2]octane, 3-butyl-1,5-dimethyl-

HRID 444114Notes

Reaction equation

HRID 444114 reaction equation
[CH2:1]([CH:5]([CH:7]1[CH:12]([CH3:13])[CH2:11][C:10]([CH3:14])=[CH:9][CH2:8]1)[OH:6])[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.C(O)(C)C>O.C1(C)C=CC=CC=1>[CH2:1]([CH:5]1[CH:7]2[CH2:8][CH2:9][C:10]([CH3:14])([CH2:11][CH:12]2[CH3:13])[O:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 86736892HCID 86736892, compound

Product 1

HCID 205615452-Oxabicyclo[2.2.2]octane, 3-butyl-1,5-dimethyl-Yield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 500 grams of alpha-n-butyl-4,6-dimethyl-3-cyclohexene methanol, 600 grams of sulfuric acid, 1400 grams of water and 500 grams of isopropyl alcohol is heated at reflux for 14 hours. The reaction mass is cooled, diluted with 1500 ml of H2O and 200 ml of toluene. The aqueous layer is discarded and the organic layer is washed twice with water, neutralizing with aqueous sodium hydroxide on the second wash. Distillation through a 1.5"×12" Goodloe column affords 351 grams of 3-n-butyl-1,5-dimethyl-2-oxabicyclo[2.2.2]octane (b.p. 90° C., 3 mm Hg pressure).

Workup

  1. temperatureat reflux for 14 hours
  2. temperatureThe reaction mass is cooled
  3. washthe organic layer is washed twice with water
  4. distillationDistillation through a 1.5"×12" Goodloe column

Sources & evidence

ORD record
ord-9c86a5243b604584bfab83cff3a16edc
Source dataset
uspto-grants-1981_04
Patent number
US04263149

Reaction notes

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