Phosphorus sulfide (P2S5) → 2-(4-Isobutylphenyl)propiononitrile

HRID 1710211Notes

Reaction equation

HRID 1710211 reaction equation
[C:1]([C:3](O)([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=1)[CH3:4])#[N:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.P12SP3(SP(SP(S3)(S1)=S)(=S)S2)=S>C1(C)C=CC=CC=1>[C:1]([CH:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:9][CH:10]=1)[CH3:4])#[N:2].[CH2:11]([C:8]1[CH:7]=[CH:6][C:5]([C:3](=[CH2:4])[C:1]#[N:2])=[CH:10][CH:9]=1)[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)2×HCID 141172Tetraphosphorus nonasulfideHCID 156283271-Cyano-1-hydroxy-1-(4-isobutylphenyl)ethane

Product 2

HCID 1083742-(4-Isobutylphenyl)propiononitrileHCID 132277082-(4-Isobutylphenyl)acrylonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A crude solution of 410 mg (2.0 mmol) of 1-cyano-1-hydroxy-1-(4-isobutylphenyl)ethane (IBACH) in 5 mL of toluene was treated under nitrogen with 450 mg (1.0 mmol) of a finely-ground commercial phosphorus pentasulfide which is a mixture of tetraphosphorus decasulfide and tetraphosphorus nonasulfide. The reaction mixture was stirred well and heated in an 85° C. bath for one hour. GC analysis of the crude reaction product indicated that the reaction resulted in the formation of 1-cyano-1-(4-isobutylphenyl)ethane (PN) and 2-(4-isobutylphenyl)acrylonitrile (UN) in a ratio of 2/1.

Workup

  1. customGC analysis of the crude reaction product

Sources & evidence

ORD record
ord-73bc2067b2d44290b2659aad313c6a6a
Source dataset
uspto-grants-1990_08
Patent number
US04952718

Reaction notes

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