Methanesulfonic Acid → 4-Isopropyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2]octane

HRID 61325Notes

Reaction equation

HRID 61325 reaction equation
[CH:1]([C:4]1([CH2:12][OH:13])[CH2:9][CH2:8][C:7]([CH3:10])=[CH:6][CH:5]1[CH3:11])([CH3:3])[CH3:2].CS(O)(=O)=O>C1(C)C=CC=CC=1>[CH:1]([C:4]12[CH2:9][CH2:8][C:7]([CH3:10])([CH2:6][CH:5]1[CH3:11])[O:13][CH2:12]2)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 56983930(1-Isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol

Product 1

HCID 897054834-Isopropyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

(1-Isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol (165 g, 0.9 mol, obtained as detailed above) was dissolved in toluene with methanesulfonic acid (MSA, 5 g, 0.05 mol). The resulting solution was heated to 70° C. and aged at 70° C. for 2 hours. GC analysis showed the completion of cyclization. The reaction mixture was cooled to room temperature, washed with sodium carbonate solution, and distilled to provide 4-isopropyl-1,5-dimethyl-2-oxa-bicyclo[2.2.2]octane.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with sodium carbonate solution
  3. distillationdistilled

Sources & evidence

ORD record
ord-d31ff57561b6429c8245f095eb6e1e51
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Reaction notes

Loading…