Reaktion #524386

Reaktionsgleichung

4-(1,1-dimethylethyl)phenol

2-chloro-N-(hydroxymethyl)acetamide

sulfuric acid

→

2-aminomethyl-4-(1,1-dimethylethyl)phenol hydrochloride

Ausbeute 51.0%

Lösungsmittel

hydrochloric acid ethanol

hydrochloric acid

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeproviding a heterogenous mixture
2. 2
   SonstigeAfter decanting the aqueous solution
3. 3
   Extraktionthe insoluble white gum is extracted with ether
4. 4
   ExtraktionThe organic extract
5. 5
   Waschenis washed with water and saturated brine
6. 6
   Sonstigeevaporated in vacuo
7. 7
   Sonstigeleaving a residual oil
8. 8
   Temperaturat reflux for 4 hours
9. 9
   Temperaturslowly cooled to -20° C
10. 10
    SonstigeThe deposited white crystalline solid is collected

Vorschrift

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.).

Quelle