Toluene → 1,3-Diphenylpropane

HRID 1967655노트

반응식

HRID 1967655 반응식
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].CN([CH2:16][CH2:17]N(C)C)C.[CH2:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O>[C:1]1([CH2:7][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH2:7][CH2:11][CH:10]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:9][CH2:8][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH2:7][CH2:11][CH:10]([C:17]2[CH:16]=[CH:3][CH:2]=[CH:1][CH:6]=2)[CH2:9][CH:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

9

반응물 5

HCID 1140TolueneHCID 7501StyreneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 178418339Butyllithium

생성물 3

HCID 141251,3-DiphenylpropaneHCID 2440201,5-Diphenylpentan-3-ylbenzeneHCID 866435581,3,5,7-Tetraphenylheptane

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A dry oil jacketed reactor equipped with stainless steel internal cooling coils (chilled water) and a glass overhead stirring mechanism (no PTFE wetted parts) was charged with 4.325 kg (51.39 mol) of anhydrous toluene and heated to 80° C. To the mixture is charged butyl lithium (0.18 mol) in cyclohexane followed by 33.47 g (0.29 mol) dry TMEDA. Styrene (1.5 g, 14.4 mol) was fed to the reactor (through a plug of anhydrous basic alumina) in 150 minutes at 90-95° C. The reaction mixture was quenched with 100 mL of water and subsequently washed three times with 0.5 kg of tap water. Toluene was distilled from the crude oligomers. The crude material was then distilled at full vacuum to yield 2.0 kg of 1,3-diphenylpropane, 300 g of 1,3,5-triphenylpentane, 120 g of 1,3,5,7-tetraphenylheptane and 8 grams of undistillable oligomer bottoms.

후처리

  1. temperaturecooling
  2. customin 150 minutes
  3. customat 90-95° C
  4. customThe reaction mixture was quenched with 100 mL of water
  5. washsubsequently washed three times with 0.5 kg of tap water
  6. distillationToluene was distilled from the crude oligomers
  7. distillationThe crude material was then distilled at full vacuum

출처 및 근거

ORD 기록
ord-68d2e45bf60e4268974eafc729877f2f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420876B2

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