反应详情

Sodium cyanide (2.94 g; 50 mmol) was slurried in methanol (20 mLs) in a 100 mL round bottom flask and the slurry was heated to a gentle reflux. To the cyanide slurry, a solution of 4-methoxymethyl-2,6-di-t-butyl phenol (12.5 g; 50 mmol), toluene (20 mLs) and methanol (25 mLs) was added dropwise over a period of time of 55 minutes. The resultant black reaction mixture was refluxed an additional 35 minutes after complete addition of the 4-methoxymethyl-2,6-di-t-butyl phenol. Upon cooling to ambient temperature, 2N hydrochloric acid (40 mLs) was added to the reaction flask. A yellow slurry which resulted was extracted with diethyl ether. The ether extract was dried (MgSO4) and concentrated in vacuo to afford 11.74 grams of 4-hydroxy-3,5-di-t-butylphenylacetonitrile as identified by NMR. Analysis by VPC indicated a 95% yield of 4-hydroxy-2,6-di-t-butylphenylacetonitrile.

1. temperaturethe slurry was heated to a gentle reflux
2. customThe resultant black reaction mixture
3. temperaturewas refluxed an additional 35 minutes
4. customA yellow slurry which resulted
5. extractionwas extracted with diethyl ether
6. extractionThe ether extract
7. dry with materialwas dried (MgSO4)
8. concentrationconcentrated in vacuo