Benzyl Alcohol → Benzyl 11-bromoundecanoate

HRID 2287280Notes

Reaction equation

HRID 2287280 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH2:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:15]([O:13][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 1781211-Bromoundecanoic acid

Product 1

HCID 289450Benzyl 11-bromoundecanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 g (113.1 mmol) of 11-bromoundecanoic acid, 18.35 g (169.7 mmol) of benzyl alcohol and 0.5 g of p-toluenesulfonic acid are heated in 200 ml of toluene for 12 hours in a water separator. It is allowed to reach room temperature, and the organic phase is washed twice with 100 ml of 5% aqueous potassium carbonate solution each. The organic phase is dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel (mobile solvent: n-hexane/acetone=30:1).

Workup

  1. customto reach room temperature
  2. washthe organic phase is washed twice with 100 ml of 5% aqueous potassium carbonate solution each
  3. customThe organic phase is dried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is chromatographed on silica gel (mobile solvent: n-hexane/acetone=30:1)

Sources & evidence

ORD record
ord-b3400b3310714d9082f6c3402de85fc3
Source dataset
uspto-grants-2000_07
Patent number
US06083479

Reaction notes

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