Cyclopentanone → HCID 67453590, compound

HRID 1441760Notes

Reaction equation

HRID 1441760 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:16])[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]#[N:15].[OH-].[K+]>>[C:1]1(=[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH3:16])[C:14]#[N:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 8452CyclopentanoneHCID 14797Potassium HydroxideHCID 311552-(o-Tolyl)acetonitrile

Product 1

HCID 67453590HCID 67453590, compoundYield 11.7%

Procedure

The procedure outlined in example 1 is repeated with cyclopentanone (14.3 g, 0.17 mol), o-tolylacetonitrile (13.1 g, 0.10 mol) and KOH (1.12 g, 0.02 mol). Short path distillation of the crude at 0.05 mbar/124-130° C. yields 5.30 g (27% yield). The product is contaminated with α,α′-dicyclopentylidenecyclopentanone. It is further purified by FC on SiO2 to yield 2.3 g of oily product (10% yield).

Workup

  1. distillationShort path distillation of the crude at 0.05 mbar/124-130° C.
  2. customyields 5.30 g (27% yield)
  3. customIt is further purified by FC on SiO2

Sources & evidence

ORD record
ord-209086fdb9274de09c6a963c18d4788b
Source dataset
uspto-grants-2010_02
Patent number
US07655701B2

Reaction notes

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