Benzhydrol → 1-(Diphenylmethoxy)-3-bromopropane

HRID 565632Notes

Reaction equation

HRID 565632 reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15][CH2:16][CH2:17][CH2:18]O.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:14][CH2:18][CH2:17][CH2:16][Br:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 123083-Bromo-1-propanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 1

HCID 143063671-(Diphenylmethoxy)-3-bromopropaneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a reactor fitted with a water trap, a mixture of benzhydrol (5.0 g), 3-bromo-1-propanol (3.8 g), camphor-10-sulfonic acid (1.0 g), and toluene (80 mL) was refluxed for 2 hours. This reaction mixture was concentrated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5) to provide 7.0 g of the title compound. Yield 85%.

Workup

  1. customIn a reactor fitted with a water trap
  2. temperaturewas refluxed for 2 hours
  3. concentrationThis reaction mixture was concentrated
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-eb4595fcf6d042379937eb0e3a74cc63
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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