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

HRID 1065558

반응식

HRID 1065558 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-142ec8df3b2c4bc792638b3f018f65c8
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04329518

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