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

HRID 1182784

Reaktionsgleichung

Reaktionsgleichung von HRID 1182784
[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/ethyl 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-39c7de63d4b24bc9bb5d85b345118a53
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664195B2

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