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

HRID 2058005Notes

Reaction equation

HRID 2058005 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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 0.5 M 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.

Workup

  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 0.5 M 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

Sources & evidence

ORD record
ord-b48cfdd1eb17427387557918472fff2b
Source dataset
uspto-grants-1980_07
Patent number
US04214004

Reaction notes

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