4-Bromophenol → 1-Bromo-4-{[(3S)-3,7-dimethyloct-6-en-1-yl]oxy}benzene

HRID 1374501Notes

Reaction equation

HRID 1374501 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[CH2:10][C@H:11]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C@@H:11]([CH3:12])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 10900106(S)-(+)-Citronellyl bromide

Product 1

HCID 693802941-Bromo-4-{[(3S)-3,7-dimethyloct-6-en-1-yl]oxy}benzeneYield 590.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-bromophenol (34.6 g, 0.20 mol), (S)-(+)-citronellyl bromide (50 g, 0.023 mol) and potassium carbonate (45 g, 0.33 mol) in butanone (500 cm3) was heated under reflux overnight. The cooled reaction mixture was filtered and the filtrate concentrated under reduced pressure. The crude product was purified by fractional distillation to yield 42.3 g (68.2%) of the desired product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. distillationThe crude product was purified by fractional distillation

Sources & evidence

ORD record
ord-2c0de2dce25b428a928ebd33fbfff6a2
Source dataset
uspto-grants-2007_01
Patent number
US07166239B2

Reaction notes

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