Sodium Carbonate → 2-(2-Pentynyl)-2-cyclopenten-1-one

HRID 267303Notes

Reaction equation

HRID 267303 reaction equation
Cl[C:2]1([CH2:10][C:11]#[C:12][CH2:13][CH3:14])[C:7](=[O:8])[CH2:6][CH2:5][CH2:4]C1=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1>[CH2:10]([C:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH:4]=1)[C:11]#[C:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 21556763HCID 21556763, compound

Product 1

HCID 110080722-(2-Pentynyl)-2-cyclopenten-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-chloro-2-(pent-2-ynyl)-cyclohexane-1,3-dione (80 g; 0.377 Mole) in dry xylene (800 ml) was allowed to reflux in the presence of anhydrous sodium carbonate (39.2 g; 0.38 Mole) until gas evolution ceased (12 h.). The reaction mixture was cooled, washed three times with water, and dried over magnesium sulfate, and the xylene was removed in vacuo. The resulting residue was distilled through a Vigreux column to afford 2-(pent-2-ynyl)-cyclopent-2-enone (41.3 g; 74 % yield), b.p. 67°-8°/0.01 Torr.

Workup

  1. custom(12 h.)
  2. temperatureThe reaction mixture was cooled
  3. washwashed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customthe xylene was removed in vacuo
  6. distillationThe resulting residue was distilled through a Vigreux column

Sources & evidence

ORD record
ord-ec32fc04256d4fb39331f6106f3795da
Source dataset
uspto-grants-1976_03
Patent number
US03941828

Reaction notes

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