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

HRID 1389954Notes

Reaction equation

HRID 1389954 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 2 1/2 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-67ecf3e6828b48bfb1be2a165405e358
Source dataset
uspto-grants-1981_01
Patent number
US04247423

Reaction notes

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