Reaktion #524390

Reaktionsgleichung

4-(1,1-dimethylpropyl)phenol

2-chloro-N-(hydroxymethyl)acetamide

water

→

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

Ausbeute 37.0%

Lösungsmittel

ethanol

acetic acid

sulfuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe solid that separates is extracted with ether
2. 2
   Extraktionthe ether extract
3. 3
   Waschenis washed with water and salt brine
4. 4
   Sonstigeevaporated to dryness
5. 5
   workup.DISSOLUTIONThe oily residue is dissolved in a mixture of 12N hydrochloric acid (100 ml.) and ethanol (100 ml.)
6. 6
   TemperaturThe mixture is refluxed for 7 hours
7. 7
   SonstigeThe mixture then is evaporated to dryness under reduced pressure
8. 8
   SonstigeThe residue is triturated with dry ether
9. 9
   Sonstigeto obtain a sticky white solid
10. 10
    Sonstigeprecipitated in the
11. 11
    workup.ADDITIONcold by addition of ether (800 ml.)
12. 12
    SonstigeThe solid is then crystallized from ethanol - 12N hydrochloric acid (1:10)

Vorschrift

A mixture of 4-(1,1-dimethylpropyl)phenol (32.8 g., 0.2 mole) and 2-chloro-N-(hydroxymethyl)acetamide (24.6 g., 0.2 mole) in acetic acid (200 ml.) and 96% sulfuric acid (20 ml.) is stirred at 20° for 12 hours and then poured into cold water (1 l.). The solid that separates is extracted with ether and the ether extract is washed with water and salt brine and evaporated to dryness. The oily residue is dissolved in a mixture of 12N hydrochloric acid (100 ml.) and ethanol (100 ml.). The mixture is refluxed for 7 hours. The mixture then is evaporated to dryness under reduced pressure. The residue is triturated with dry ether to obtain a sticky white solid that is dissolved in hot ethanol (50 ml.) and precipitated in the cold by addition of ether (800 ml.). The solid is then crystallized from ethanol - 12N hydrochloric acid (1:10) to obtain 2-aminomethyl-4-(1,1-dimethylpropyl)phenol hydrochloride (17 g.), m.p. 191°-192° C.

Quelle