Sulfuric Acid → 2-(Aminomethyl)-4-tert-butylphenol hydrochloride

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 4-(1,1-dimethylethyl)phenol (75 g., 0.50 mole), 2-chloro-N-(hydroxymethyl)acetamide (61 g., 0.50 mole) and 96% sulfuric acid (50 ml.) in acetic acid (500 ml.) is stirred at 20° C. for 4 hours and then poured into ice water (2 l.) providing a heterogenous mixture. After decanting the aqueous solution, the insoluble white gum is extracted with ether. The organic extract is washed with water and saturated brine and evaporated in vacuo leaving a residual oil. A solution of the latter in 12N hydrochloric acid-ethanol (1:1; 400 ml.) is heated at reflux for 4 hours, diluted with 12N hydrochloric acid (200 ml.) and slowly cooled to -20° C. The deposited white crystalline solid is collected to provide pure 2-aminomethyl-4-(1,1-dimethylethyl)phenol hydrochloride (55 g.), m.p. 227°-229° C. (dec.).

Herkunft & Nachweise