Cyclohexanone → HCID 12862446, compound

HRID 1441759Notes

Reaction equation

HRID 1441759 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([CH3:17])[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.[OH-].[K+]>>[C:1]1(=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([CH3:17])=[CH:9][CH:10]=2)[C:15]#[N:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 7967CyclohexanoneHCID 14797Potassium HydroxideHCID 76280p-Tolylacetonitrile

Product 1

HCID 12862446HCID 12862446, compoundYield 63%

Procedure

The procedure outlined in example 1 is repeated with cyclohexanone (22.34 g, 0.29 mol), p-tolylacetonitrile (20.96 g, 0.16 mol) and KOH (1.79 g, 0.032 mol). Short path distillation of the crude at 0.05 mbar/115-130° C. followed by recrystallization from hexane yields 21.1 g (63% yield) of product as white crystals, m.p. 50.5-51.3° C.

Workup

  1. distillationShort path distillation of the crude at 0.05 mbar/115-130° C.
  2. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-963ebf937d3e47398e1370745a449557
Source dataset
uspto-grants-2010_02
Patent number
US07655701B2

Reaction notes

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