Toluene → 1,3-Diphenylpropane

HRID 71079ノート

反応式

HRID 71079 の反応式
[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

参加物

9

反応物 5

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

生成物 3

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A dry oil-jacketed reactor equipped with stainless steel internal cooling coils (chilled water) and a glass overhead stiffing 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.

後処理

  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

出典と根拠

ORDレコード
ord-778209de1fd14026bddaab9e882e112e
出典データセット
uspto-grants-2014_09
特許番号
US08822743B2

反応ノート

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