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

HRID 1160152

Reaction equation

HRID 1160152 reaction equation
[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]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 231125733-Phenyl-3-hydroxypropylmethanesulfonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a1f7f9b8e63145dfac4d3a9f42460c36
Source dataset
uspto-grants-2010_10
Patent number
US07816345B2

Linked notes

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