p-Toluenesulfonic acid → Octa-1,3,5-triene

HRID 443190Notes

Reaction equation

HRID 443190 reaction equation
[NH:1]1[CH2:6][CH2:5]OCC1.CCN(CCO[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][C:22]2C=CC=CC=2)=[CH:19][CH:20]=1)CC.Cl.[C:29]1(C)[CH:34]=[CH:33][C:32](S(O)(=O)=O)=[CH:31][CH:30]=1.C=CC=C>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2].CO>[CH2:17]=[CH:16][CH:15]=[CH:20][CH:19]=[CH:18][CH2:21][CH3:22].[CH:6]([NH2:1])=[CH:5][CH:34]=[CH:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 78451,3-ButadieneHCID 8083MorpholineHCID 175534Tesmilifene Hydrochloride

Product 2

HCID 182132Octa-1,3,5-trieneHCID 73866044Aminooctadiene

Reagents, catalysts & solvents 2

HCID 5486778Palladium acetylacetonateCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 8.70 g (100 mmol) of morpholine, 0.076 (0.25 mmol) of Pd(acac)2 (acac=acetylacetonate), and 0.35 g (0.875 mmol) of DPPE was admixed with 0.141 g of p-toluenesulfonic acid and 2.4 g of methanol. After forcing in 5.4 g (100 mmol) of butadiene, the mixture was stirred for 17 h at 100° C. under autogenous pressure. There is obtained a yield of 96% at a selectivity of 1 percent by area of octatriene, 3 percent by area of (3,N)-(but-1-enyl)morpholine, 94 percent by area of (1,N)-(but-2-enyl)-morpholine, 1 percent by area of octadienylamine and 1 percent by area of by-products.

Sources & evidence

ORD record
ord-f1463e3bd0404c3bbaa9f90d5c44228a
Source dataset
uspto-grants-1999_04
Patent number
US05892125

Reaction notes

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