Ammonium Hydroxide → 3-Amino-1-phenylpropan-1-ol

HRID 1271591

Reaktionsgleichung

Reaktionsgleichung von HRID 1271591
[C:1]1([CH:7]([OH:15])[CH2:8][CH2:9]CS([O-])(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+:17]>O1CCCC1>[NH2:17][CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:15]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 231125733-Phenyl-3-hydroxypropylmethanesulfonate

Produkt 1

HCID 1215483-Amino-1-phenylpropan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 3-phenyl-3-hydroxypropylmethanesulfonate (1.71 g, Gao, et al., J. Org. Chem., 1988, 53, 4081), tetrahydrofuran (10 mL) and 28% ammonium hydroxide (30 mL) was heated in a bomb at 65° C. for 16 hours. After cooling, the volatiles were eliminated to leave the aqueous solution which was extracted with ether. The aqueous layer was concentrated under reduced pressure, azeotroped twice with anhydrous acetonitrile and dried under vacuum to give 3-amino-1-phenyl-1-propanol (1.04 g) as a white solid: mp 92–94° C., Rf=0.1 (silica, methanol/ehtyl acetate 1/1).

Aufarbeitung

  1. temperatureAfter cooling
  2. customto leave the aqueous solution which
  3. extractionwas extracted with ether
  4. concentrationThe aqueous layer was concentrated under reduced pressure
  5. customazeotroped twice with anhydrous acetonitrile
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-06006a27c0ee453c9b1b772a1c6c8605
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205404B1

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