1,3-Benzenediacetonitrile, 5-(hydroxymethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl- → 2-[3-(2-Cyanopropan-2-yl)-5-formylphenyl]-2-methylpropanenitrile

HRID 2107762Notes

Reaction equation

HRID 2107762 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:6]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:8]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:2]([C:3]1[CH:8]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:6]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 193493981,3-Benzenediacetonitrile, 5-(hydroxymethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-HCID 178418287HCID 178418287, compound

Product 1

HCID 115069812-[3-(2-Cyanopropan-2-yl)-5-formylphenyl]-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2'-(5-hydroxymethyl-1,3-phenylene)di(2-methylpropiononitrile), (1.9 g), in dichloromethane (20 ml) was treated with pyridinium chlorochromate (2.15 g) and stirred at room temperature for 1.5 h. The reaction mixture was subjected to flash column chromatography, eluting with dichloromethane, to give 2,2'-(5-formyl- 1,3-phenylene)di(2-methylpropiononitrile), mp. 145°-147°.

Workup

  1. washeluting with dichloromethane

Sources & evidence

ORD record
ord-e9822b04408541c78c6f630dcdefbd99
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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