Water → Benzenemethanol,2-pentyl-

HRID 2082194Notes

Reaction equation

HRID 2082194 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10].BrCCCC.O>CCCCCC.CCOCC>[CH2:6]([C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10])[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 69942-Methylbenzyl alcoholHCID 8002Butyl bromideHCID 178418339Butyllithium

Product 1

HCID 10058085Benzenemethanol,2-pentyl-

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
24 °C

Procedure

245 ml of a 1.6 molar butyllithium solution in hexane is instilled in a solution of 20.0 g of 2-methylbenzyl alcohol in 185 ml of ether under argon, so that the temperature does not exceed 10° C. Then, it is refluxed for 5 hours, allowed to cool off to 24° C., 22.4 g of 1-bromobutane is instilled and it is stirred for 16 hours at 24° C. The reaction mixture is added to 100 ml of water and extracted three times with 100 ml of ether each. The organic phase is washed with brine, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with hexane/0-30% of ethyl acetate. 20.1 g o the title compound is obtained as a colorless oil.

Workup

  1. customdoes not exceed 10° C
  2. temperatureThen, it is refluxed for 5 hours
  3. extractionextracted three times with 100 ml of ether each
  4. washThe organic phase is washed with brine
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe residue is chromatographed on silica gel with hexane/0-30% of ethyl acetate

Sources & evidence

ORD record
ord-355ca619808b468b8b10174278a15356
Source dataset
uspto-grants-1993_02
Patent number
US05187286

Reaction notes

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