1,3-Butadiene → HCID 537535, compound

HRID 2051635Notes

Reaction equation

HRID 2051635 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].C=[CH:11][C:12](=[O:18])CCCC=C.C=CC=C>C(O)(=O)C>[C:12]([O:9][CH:3]([CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8])[CH:2]=[CH2:1])(=[O:18])[CH3:11]

Participants

5

Reactant 3

HCID 78451,3-ButadieneHCID 5457381,7-Octadien-3-olHCID 118047521,7-octadien-3-one

Product 1

HCID 537535HCID 537535, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,7-Octadien-3-ol, Compound (III), which is the starting material for preparing 1,7-octadien-3-one of this invention can easily be synthesized by dimerizing butadiene using a palladium complex as a catalyst in the presence of acetic acid to obtain 3-acetoxy-1,7-octadiene, Compound (I), and then hydrolyzing the same. (See Tetrahedron Letters, No. 26, page 2451, 1967 incorporated herein by reference which teaches the synthesis of 4-acetoxy-2,7-octadiene and 1-acetoxy-2,7-octadiene by dimerizing butadiene in the presence of a bis(triphenyl phosphine) (maleic anhydride) palladium catalyst and acetic acid at 120° C.)

Workup

  1. customcan easily be synthesized

Sources & evidence

ORD record
ord-5c251e8d37ec45118948c4b87c67d129
Source dataset
uspto-grants-1980_01
Patent number
US04181683

Reaction notes

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