Toluene → 1163-13-9

HRID 637907Notes

Reaction equation

HRID 637907 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[CH:5][C:4]=1[CH3:14].[H-].[K+].C(Br)/[CH:18]=[C:19](/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])\[CH3:20].[C:28]1(C)C=CC=CC=1>>[CH3:28][C:5]1[C:6](=[O:13])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:2])[C:4]=1[CH2:14]/[CH:18]=[C:19](/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])\[CH3:20]

Participants

5

Reactant 4

HCID 1140TolueneHCID 82127Potassium hydrideHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-HCID 11229228HCID 11229228, compound

Product 1

HCID 52803741163-13-9

Procedure

To dry toluene (40) are added 4-methoxy-3-methyl-1-naphthol (1.88 g) and potassium hydride (401 mg) followed by refluxing in nitrogen streams for an hour. After spontaneous cooling, geranyl bromide (1.95 g) is added and the mixture is stirred at room temperature for 24 hours. To the reaction mixture is added petroleum ether (100 ml) and the precipitated potassium bromide is filtered off and the solvent is distilled off at room temperature and under reduced pressure. The residue is dissolved in dimethylformamide (50 ml) followed by addition of bis(salicylidene)ethylenediiminocobalt(II) (100 mg). The mixture is stirred in oxygen gas streams at atmospheric temperature and pressure for one hour, after which the product is extracted with ether. The ethereal layer is washed with water and dried over anhydrous sodium sulfate, followed by distillation removal of the solvent. The residue is fractionally purified by silica gel column chromatography (developing solvent:ether-petroleum ether=1:19). The crude crystals thus obtained are recrystallized from acetone-alcohol. The above procedure yields menaquinone-2 (1.45 g) as yellow needles melting at 51° C.-53° C.

Workup

  1. temperatureby refluxing in nitrogen streams for an hour
  2. filtrationthe precipitated potassium bromide is filtered off
  3. distillationthe solvent is distilled off at room temperature and under reduced pressure
  4. dissolutionThe residue is dissolved in dimethylformamide (50 ml)
  5. additionfollowed by addition of bis(salicylidene)ethylenediiminocobalt(II) (100 mg)
  6. stirringThe mixture is stirred in oxygen gas streams at atmospheric temperature and pressure for one hour
  7. extractionafter which the product is extracted with ether
  8. washThe ethereal layer is washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationfollowed by distillation removal of the solvent
  11. customThe residue is fractionally purified by silica gel column chromatography (developing solvent:ether-petroleum ether=1:19)
  12. customThe crude crystals thus obtained
  13. customare recrystallized from acetone-alcohol

Sources & evidence

ORD record
ord-58bc8c4680a446cfaf5619970f448cca
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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