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

HRID 2286369Notes

Reaction equation

HRID 2286369 reaction equation
[CH2:1]([CH:5]([CH:7]1[CH:12]([CH3:13])[CH2:11][CH:10]([CH3:14])[CH2:9][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 23463247HCID 23463247, compound

Product 1

HCID 205615452-Oxabicyclo[2.2.2]octane, 3-butyl-1,5-dimethyl-Yield 70.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 500 grams of alpha-n-butyl-4,6-dimethyl-3-cyclohexane 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-4f2257fe173a4b90b1a9a9011f924281
Source dataset
uspto-grants-1981_05
Patent number
US04265923

Reaction notes

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