Acetone → Cyclopentanol, acetate

HRID 263138Notes

Reaction equation

HRID 263138 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][CH2:8][CH:7]=[CH:6]1)(=[O:3])[CH3:2].ClC1C=CC=CC=1.[OH-].CC(C)=O>CO>[C:1]([O:4][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 961HydroxideHCID 7964ChlorobenzeneHCID 140735Acetic acid, cyclopent-2-en-1-yl ester

Product 1

HCID 70273Cyclopentanol, acetateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
56 °C

Procedure

A solution of 1.80 g (0.014 mol) of 2-cyclopentenyl acetate in 3.80 g (0.12 mol) of methanol and 0.700 g of chlorobenzene (the internal standard for chromatographic analysis) was slowly passed through a jacketed column containing 20 ml of Dowex 1-X4 (an anion exchange resin of the quaternary ammonium type) in the hydroxide form in methanol. The column was maintained at 56° C. by refluxing acetone in the jacket. The resin was then rinsed with methanol, and the combined effluent and rinsings were analyzed by gas chromatography using a 6-ft. OV-17 column programmed from 80° to 220° C. The analysis showed that 2-cyclopentenol had been formed in 96% yield and essentially 100% efficiency. No by-products were observed.

Workup

  1. washThe resin was then rinsed with methanol
  2. customprogrammed from 80° to 220° C
  3. customhad been formed in 96% yield and essentially 100% efficiency

Sources & evidence

ORD record
ord-5911146e230d4528b94a170bd145a9dd
Source dataset
uspto-grants-1979_05
Patent number
US04156097

Reaction notes

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