O-Xylene → 5-Ortho-tolylpentene

HRID 258638Notes

Reaction equation

HRID 258638 reaction equation
[Na].[K].CN(CCN(C)C)C.[CH2:11]=[CH:12][CH:13]=[CH2:14].[C:15]1([CH3:22])[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1>O>[CH3:11][C:12]1[C:20]([CH2:19][CH2:18][CH2:17][CH:16]=[CH2:21])=[CH:15][CH:22]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 7237O-XyleneHCID 78451,3-ButadieneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 5360545SodiumHCID 5462222Potassium

Product 1

HCID 108774255-Ortho-tolylpenteneYield 59.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the equipment and procedure described in Example I a run was made using an alloy of 0.1% sodium and 0.1% potassium based on the weight of the xylene and another run with the same alloy was made adding 0.09% TMEDA. Both runs were made using butadiene having 155 ppm water which decreased activity but the effect of the amine cocatalyst is indicated by a trans:cis ratio 2.11 compared to 1.35 for the alloy alone, and by cumulative yield of 59.7% 5-OTP compared to 40% for the alloy alone. Other examples are listed in Table I.

Sources & evidence

ORD record
ord-70032d0228f64b2584c66eaf46f1e85e
Source dataset
uspto-grants-1977_07
Patent number
US04034052

Reaction notes

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