Benzhydrol → 2-Amino-1-diphenylmethoxy-2-methylpropane

HRID 1613184Notes

Reaction equation

HRID 1613184 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH:7](O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][O:4][CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 118072-Amino-2-methyl-1-propanolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 197753022-Amino-1-diphenylmethoxy-2-methylpropaneYield 69.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-2-methylpropanol (89.1 g), benzhydrol (190 g) and para-toluenesulphonic acid monohydrate (200 g) in toluene (1200 ml) was heated under reflux in a Dean-Stark apparatus for four hours and evaporated. The residue was partitioned between ether and water and the organic layer was washed with water and extracted into 10% aqueous citric acid. The acidic extract was washed with ether, basified with solid sodium carbonate and extracted into ether. The organic extract was washed with water, dried over sodium sulphate and evaporated to give the title compound as a pale yellow oil (177 g, 69%) which was characterised by its 1H-n.m.r. spectrum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a Dean-Stark apparatus for four hours
  3. customevaporated
  4. customThe residue was partitioned between ether and water
  5. washthe organic layer was washed with water
  6. extractionextracted into 10% aqueous citric acid
  7. extractionThe acidic extract
  8. washwas washed with ether
  9. extractionextracted into ether
  10. extractionThe organic extract
  11. washwas washed with water
  12. dry with materialdried over sodium sulphate
  13. customevaporated

Sources & evidence

ORD record
ord-62721b2bbdd94ffda5d2117873e8a9c7
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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