Toluene → 1,3-Diphenylpropane

HRID 71079Notes

Reaction equation

HRID 71079 reaction equation
[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

Participants

9

Reactant 5

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

Product 3

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-778209de1fd14026bddaab9e882e112e
Source dataset
uspto-grants-2014_09
Patent number
US08822743B2

Reaction notes

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