Water → 2-Cyclohexenyl 2-cyclopentenyl ether

HRID 2163496Notes

Reaction equation

HRID 2163496 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][CH2:8][CH:7]=[CH:6]1)(=O)[CH3:2].[CH:10]1(O)[CH2:15]CC[CH:12]=[CH:11]1.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH:5]1([O:4][CH:1]2[CH2:12][CH2:11][CH2:10][CH:15]=[CH:2]2)[CH2:9][CH2:8][CH:7]=[CH:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 131982-Cyclohexen-1-OLHCID 140735Acetic acid, cyclopent-2-en-1-yl ester

Product 1

HCID 213182372-Cyclohexenyl 2-cyclopentenyl ether

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

A two-phase reaction mixture containing 2-cyclopentenyl acetate (0.30 g, 2.4 millimols), 2-cyclohexenol (0.50 g, 5.1 millimols), tetrabutylammonium hydrogen sulfate (0.020 g, 0.06 millimols), and water (0.25 g, 13.9 millimols) was heated at 40° C with vigorous stirring for four hours. Acetone was then added to give a one-phase system for analytical purposes, and the solution was analyzed by gas chromatography using an Apiezon column programmed from 60 to 220° C. The following relative peak areas were observed for the cyclic components:

Workup

  1. customA two-phase reaction mixture
  2. customto give a one-phase system for analytical purposes
  3. customprogrammed from 60 to 220° C

Sources & evidence

ORD record
ord-2afbd30e6e80446d9c0d0d9e068a7b58
Source dataset
uspto-grants-1979_01
Patent number
US04134924

Reaction notes

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