Toluene → 3-(4-Bromophenyl)propan-1-ol

HRID 2120550Notes

Reaction equation

HRID 2120550 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[H][H]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 40481813-(4-bromophenyl)prop-2-yn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 105606143-(4-Bromophenyl)propan-1-olYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution under inert gas of 36.4 g of 3-(4-bromophenyl)-2-propynol (stage A) in 200 ml of ethanol at 5% of toluene, is added 200 ml of toluene, 7.9 g of Wilkinson's reagent and hydrogen at 1900 mbar for 5 hours. It is evaporated at reduced pressure until the obtainment of 45.9 g of raw product that is purified by chromatography on silica by eluting with the compound CH2Cl2/AcOEt 95/5. 30.1 g of expected product is obtained. Rf (CH2Cl2/AcOEt 95/5): 0.28 IR (CHCl3)

Workup

  1. customIt is evaporated at reduced pressure until the obtainment of 45.9 g of raw product that
  2. customis purified by chromatography on silica
  3. washby eluting with the compound CH2Cl2/AcOEt 95/5

Sources & evidence

ORD record
ord-f73728e968044fea9bd017ebb80e238d
Source dataset
uspto-grants-2004_02
Patent number
US06693090B2

Reaction notes

Loading…