Dimethyl Sulfoxide → 2-(4-Methyl-phenoxy)-5-methyl-phenylacetonitrile

HRID 1111795Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH3:17])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.CS(C)=O.[C-:22]#[N:23].[Na+]>O>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([CH3:17])=[CH:4][C:3]=2[CH2:2][C:22]#[N:23])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 36 °C

Procedure

A solution of 108 g. of 3-chloromethyl-4-(4-methyl-phenoxy)-toluene in 70 ml. of dimethylsulfoxide is added dropwise at 20°-25° C. to a suspension of 23 g. of sodium cyanide in 35 ml. of dimethylsulfoxide. The mixture is subsequently stirred for 4 hours at 36° C., then diluted with 1 liter of water and extracted three times with benzene. The benzene extracts are washed three times with water, then dried over sodium sulfate and evaporated in vacuo, and there is obtained crude 2-(4-methyl-phenoxy)-5-methyl-phenylacetonitrile as a brown oil.

Workup

extractionextracted three times with benzene
washThe benzene extracts are washed three times with water
dry with materialdried over sodium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-30d070ebd3414a89b0e418f5fea9bb16
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04118572

Reaction notes

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