Acetic Acid → Isopentylidene cyclopentanone

HRID 61330Notes

Reaction equation

HRID 61330 reaction equation
[OH-].[Na+].[C:3]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH:9](=O)[CH2:10][CH:11]([CH3:13])[CH3:12].C(O)(=O)C>O>[CH3:12][CH:11]([CH3:13])[CH2:10][CH:9]=[C:4]1[CH2:5][CH2:6][CH2:7][C:3]1=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 115523-MethylbutanalHCID 14798Sodium Hydroxide

Product 1

HCID 54327707Isopentylidene cyclopentanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Water (1.9 L) and sodium hydroxide (NaOH, 40 g, 50% caustic) were charged in a flask and heated to 80° C. A premix of cyclopentanone (840 g, 10 mol) and isovaleraldehyde (1.05 Kg, 12 mol) was slowly fed for over 5 hours. The reaction mixture was aged at 80° C. for another 30 minutes, cooled to room temperature, and quenched with acetic acid (120 g, 2 mol). A rushover process provided the crude product 2-[3-methyl-butylidene]-cyclopentanone.

Workup

  1. customwas slowly fed for over 5 hours
  2. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-1081c40ca32748ed83bb35a3d586dc86
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Reaction notes

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