Hydrochloric Acid → 1,5-Dimethyl 3-isopropyl-2-oxabicyclo[2.2.2]octane

HRID 1732531Notes

Reaction equation

HRID 1732531 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[CH:9]([CH:11]([CH3:13])[CH3:12])[OH:10].C(O)(C)C.Cl.O>C1(C)C=CC=CC=1>[CH3:8][C:6]12[CH2:5][CH2:4][CH:3]([CH:2]([CH3:1])[CH2:7]1)[CH:9]([CH:11]([CH3:13])[CH3:12])[O:10]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3776IsopropanolHCID 205615382,4-Dimethyl-alpha-isopropyl-3-cyclohexene methanol

Product 1

HCID 205615371,5-Dimethyl 3-isopropyl-2-oxabicyclo[2.2.2]octaneYield 19.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 130 grams of 2,4-dimethyl-alpha-isopropyl-3-cyclohexene methanol, 300 grams of isopropyl alcohol and 1000 ml of concentrated HCl is heated 21/2 hours at reflux. The reaction mass is cooled and 1500 ml of H2O and 100 ml of toluene is added with stirring. The aqueous layer is discarded and the organic layer is washed twice with water, neutralizing with aqueous caustic soda on the second wash. The organic layer is distilled through a 48" Vigreux column affording 25 grams of 1,5-dimethyl-3-isopropyl-2-oxabicyclo[2.2.2]octane (b.p. 55° C., 1.8 mm Hg pressure).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mass is cooled
  3. washthe organic layer is washed twice with water
  4. distillationThe organic layer is distilled through a 48" Vigreux column

Sources & evidence

ORD record
ord-10e223d3a498450bb2c9efbfc62c8c0f
Source dataset
uspto-grants-1980_12
Patent number
US04238344

Reaction notes

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