Toluene → 4,4'-Bis(4-methylbenzyl)-1,1'-biphenyl

HRID 2035285

반응식

HRID 2035285 반응식
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Ti](Cl)(Cl)(Cl)Cl.C(O)C>[CH3:23][C:17]1[CH:22]=[CH:21][C:20]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][C:12]([CH2:15][C:6]4[CH:7]=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=4)=[CH:11][CH:10]=3)=[CH:5][CH:4]=2)=[CH:19][CH:18]=1

참가 물질

5

반응물 2

HCID 1140TolueneHCID 742754,4'-Bis(chloromethyl)-1,1'-biphenyl

생성물 1

HCID 205909844,4'-Bis(4-methylbenzyl)-1,1'-biphenyl

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 702Ethanol용매

실험 절차

A 500 mL flask was charged with 4,4′-bis(chloromethyl)-1,1′-biphenyl (25.1 g) and toluene (300 mL). To the clear solution stirring at room temperature was added titanium tetrachloride (1 mL) and the mixture instantly became dark brown. After 5 minutes, a second 1 mL aliquot of catalyst was added. After stirring overnight at room temperature, ethanol (10 mL) was added to kill the catalyst, and the mixture became a light, cream colored suspension. The organic layer was concentrated to dryness under vacuum on a rotary evaporator. The tan solid was suspended in 200 mL boiling toluene and treated with MgSO4. Vacuum filtration through glass fiber filter paper gave a clear solution to which 200 mL heptane was added while hot. The slightly turbid solution was cooled to room temperature, then in a freezer overnight to complete crystallization. White crystals, 17.4 g, mp=161.8 C, were recovered. GC/MS, HNMR, CNMR and IR were all consistent with the desired product.

후처리

  1. additiona second 1 mL aliquot of catalyst was added
  2. stirringAfter stirring overnight at room temperature
  3. concentrationThe organic layer was concentrated to dryness under vacuum on a rotary evaporator
  4. additiontreated with MgSO4
  5. filtrationVacuum filtration through glass fiber
  6. filtrationfilter paper
  7. customgave a clear solution to which 200 mL heptane
  8. additionwas added while hot
  9. temperatureThe slightly turbid solution was cooled to room temperature
  10. waitin a freezer overnight to complete
  11. customcrystallization
  12. customWhite crystals, 17.4 g, mp=161.8 C, were recovered

출처 및 근거

ORD 기록
ord-142a94cea641463989cee6fa590fd6a8
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08574323B2

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