1,3-Dibromopropane → 2-[4-(3-Bromopropoxy)phenyl]ethanol

HRID 2109686Notes

Reaction equation

HRID 2109686 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][CH2:19][CH2:20]Br>C(#N)C>[Br:17][CH2:18][CH2:19][CH2:20][O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 218806552-[4-(3-Bromopropoxy)phenyl]ethanolYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-hydroxyphenethyl alcohol (4.37 g, 31.0 mmol) and potassium carbonate (6.55 g, 47.0 mmol) in acetonitrile (62.0 mL) was added 1,3 dibromopropane (31.0 mL, 316 mmol). The reaction mixture was heated to 70° C. for 12 hours and then cooled to room temperature, filtered and concentrated under vacuum. The resulting oil was purified by silica gel chromatography using a mixture of 4:1 hexanes and ethyl acetate to give the title compound (6.21 g) as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe resulting oil was purified by silica gel chromatography
  5. additiona mixture of 4:1 hexanes and ethyl acetate

Sources & evidence

ORD record
ord-9330e65836d3494da5605b21d25a604c
Source dataset
uspto-grants-2009_04
Patent number
US07514558B2

Reaction notes

Loading…