Benzene → [1,1'-Biphenyl]-3-methanol, 2-methyl-

HRID 485539

Reaktionsgleichung

Reaktionsgleichung von HRID 485539
I[C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[CH3:10][C:3]1[C:4]([CH2:5][OH:6])=[CH:7][CH:8]=[CH:9][C:2]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 24477Sodium ThiosulfateHCID 15035506(3-Iodo-2-methylphenyl)methanol

Produkt 1

HCID 596875[1,1'-Biphenyl]-3-methanol, 2-methyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In a photoreactor was placed 3-iodo-2-methylbenzyl alcohol (5.0 g, 0.02 mole) and 800 ml of benzene. To this was added sodium thiosulfate (5.0 g, 0.04 mole) in 15 ml of water. The mixture was purged with argon for 30 minutes, then irradiated with a 200 watt medium pressure ultraviolet lamp for 36.5 hours. The reaction mixture was then transferred to a separatory funnel. The photoreactor was washed with approximately 20 ml each of water, chloroform, and acetone. These washes were added to the separatory funnel. The organic layer was washed with aqueous 0.5M sodium thiosulfate, then with an aqueous solution saturated with sodium chloride. The organic layer was then dried and filtered. The filtrate was evaporated under reduced pressure to an oily residue. The residue was purified by column chromatography on silica gel, elution with 1:1 hexane:chloroform, to give 2-methyl[1,1'-biphenyl]-3-methanol (2.4 g). The nmr and ir spectra were consistent with that expected for the named compound.

Aufarbeitung

  1. customThe mixture was purged with argon for 30 minutes
  2. customirradiated with a 200 watt medium pressure ultraviolet lamp for 36.5 hours
  3. customThe reaction mixture was then transferred to a separatory funnel
  4. washThe photoreactor was washed with approximately 20 ml each of water, chloroform, and acetone
  5. additionThese washes were added to the separatory funnel
  6. washThe organic layer was washed with aqueous 0.5M sodium thiosulfate
  7. customThe organic layer was then dried
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure to an oily residue
  10. customThe residue was purified by column chromatography on silica gel, elution with 1:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-c2877e1f0361462fb672744e41337c9b
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536591

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