Toluene → 2-Isopentylcyclopent-2-en-1-one

HRID 61331

Reaction equation

HRID 61331 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[C:19]1(C)C=CC=CC=1>>[CH3:19][CH:8]([CH3:18])[CH2:13][CH2:12][C:11]1[C:5](=[O:7])[CH2:6][CH2:9][CH:10]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7918Acetic Anhydride

Product 1

HCID 1224642-Isopentylcyclopent-2-en-1-one

Conditions

Temperature
125 °C

Procedure

2-(3-Methyl-butyllidene)-cyclopentanone (1.093 Kg, 7.19 mol, obtained as detailed above), acetic anhydride (300 mL, 3.17 mol), p-toluenesulfonic acid (PTSA, 10 g), and toluene (500 mL) were charged into a flask and heated to 120-130° C. When gas chromatography analysis indicated the completion of the reaction, the reaction mixture was cooled to room temperature and quenched with Na2CO3 solution (100 mL). The resulting mixture was washed twice with brine (1 L). A rushover process provided the crude product 2-(3-methyl-butyl)-cyclopent-2-enone.

Workup

  1. customthe completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customquenched with Na2CO3 solution (100 mL)
  4. washThe resulting mixture was washed twice with brine (1 L)

Sources & evidence

ORD record
ord-f38a1f5c245a4e0ebbe5d8bd9cdd9f36
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Linked notes

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