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

HRID 1636800Notes

Reaction equation

HRID 1636800 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-98e88713cc7344dcb6b3a4a65cfdacad
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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