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

HRID 1451583Notes

Reaction equation

HRID 1451583 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[OH:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][OH:23])[CH:17]=[CH:18][CH:19]=1>C(O)C>[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][OH:23])[CH:17]=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 127441-BromoundecaneHCID 103518713-Hydroxybenzenepropanol

Product 1

HCID 218493913-(3-Undecyloxyphenyl)propanolYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A 15N 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-ccc3239ea2c14fc994911ecea863df2b
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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