Réaction #6825

Équation de réaction

hydrochloric acid

4-hydroxyphenylacetone

ammonium acetate

sodium cyanoborohydride

→

4-(2-amino-propyl)-phenol

Rendement 56.2%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was evaporated
2. 2
   workup.DISSOLUTIONthe resulting residue was dissolved in water
3. 3
   Extractionextracted 3 times with diethyl ether
4. 4
   workup.ADDITIONThe aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide
5. 5
   Extractionextracted with diethyl ether
6. 6
   SéchageThe basic ether layer was dried over sodium sulfate
7. 7
   Autrethe solvent was removed in vacuo

Mode opératoire

To a solution of 4-hydroxyphenylacetone (0.5 g, Avocado, U.K.) and ammonium acetate (2.54 g, Aldrich, U.S.A.) in 10 mL methanol was added 0.17 g of sodium cyanoborohydride (Aldrich, U.S.A.). After stirring for 72 h at rt, concentrated hydrochloric acid was added dropwise until the solution reached pH 2. The solvent was evaporated and the resulting residue was dissolved in water, then extracted 3 times with diethyl ether. The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide and extracted with diethyl ether. The basic ether layer was dried over sodium sulfate and the solvent was removed in vacuo to give 0.23 g of 4-(2-amino-propyl)-phenol.

Source