1-Bromoundecane → 3-(3-Undecyloxyphenyl)propanol

HRID 617843Notes

Reaction equation

HRID 617843 reaction equation
[OH-].[Na+].[CH2:3](Br)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH:15][C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][CH2:24][OH:25])[CH:19]=[CH:20][CH:21]=1>C(O)C>[CH2:3]([O:15][C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][CH2:24][OH:25])[CH:19]=[CH:20][CH:21]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 127441-BromoundecaneHCID 14798Sodium HydroxideHCID 103518713-Hydroxybenzenepropanol

Product 1

HCID 218493913-(3-Undecyloxyphenyl)propanolYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A 15 N aqueous sodium hydroxide solution (2 ml) and a solution (10 ml) of 8.0 g of undecyl bromide in ethanol was added to a solution (30 ml) of 4.56 g of 3-(3-hydroxyphenyl)propanol in ethanol and the mixture was stirred at 70° C. for 12 hours. The solvent was distilled away and the residue was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogencarbonate and brine, and dried over magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20-1:3) to give 7.37 g of 3-(3-undecyloxyphenyl)propanol as a colorless, oily substance.

Workup

  1. distillationThe solvent was distilled away
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with saturated sodium hydrogencarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled away
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20-1:3)

Sources & evidence

ORD record
ord-e0f8219bd03d4a219f95efeed23daeb0
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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