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

HRID 1361409Notes

Reaction equation

HRID 1361409 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-00cb1527b6d74c5a864d5f50ab922650
Source dataset
uspto-grants-2011_02
Patent number
US07879879B2

Reaction notes

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