Reaktion #954367

Reaktionsgleichung

hydrochloric acid

toluene

4-dimethylamino-3,5-di-isopropylphenylthiocyanate

mercaptophenol

sodium hydroxide

2-bromo-hexanoic acid

→

product

2-((4-(dimethylamino)-3,5-bis(1-methylethyl)phenyl)thio)-hexanoic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared above 200 ml
2. 2
   workup.ADDITIONThe mixture was then treated with 100 ml
3. 3
   SonstigeThe resulting layers were separated
4. 4
   Waschenthe toluene was washed twice
5. 5
   TrocknenThe organic layers were dried over Na2SO4
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto leave a light yellow oil
8. 8
   Sonstigecrystallized
9. 9
   WaschenThe crystals of 2-((4-(di-methylamino)-3,5-bis(1-methylethyl)phenyl)thio)-hexanoic acid were washed with cold pentane
10. 10
    Sonstigesucked dry on a suction
11. 11
    Filtrationfilter

Vorschrift

To the toluene solution containing the mercaptophenol prepared above 200 ml. of 20% sodium hydroxide and 7.4 grams of 2-bromo-hexanoic acid were added. The reaction mass was stirred at room temperature for about one hour. The mixture was then treated with 100 ml. of 1 N hydrochloric acid. The resulting layers were separated and the toluene was washed twice or until neutral. The organic layers were dried over Na2SO4 and evaporated to leave a light yellow oil weighing 13.4 grams which crystallized on standing. The crystals of 2-((4-(di-methylamino)-3,5-bis(1-methylethyl)phenyl)thio)-hexanoic acid were washed with cold pentane and sucked dry on a suction filter to give 3.14 grams of product. The melting point was found to be 66°-68° C. Infrared and NMR analysis confirmed the structure.

Quelle