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

HRID 900222

Reaction equation

HRID 900222 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-cabd3098ed874b72920ab60b6b22771f
Source dataset
uspto-grants-2008_04
Patent number
US07358244B2

Linked notes

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