beta-Bromostyrene → 6-Phenyl-3,5-hexadienoic acid

HRID 1105534Notes

Reaction equation

HRID 1105534 reaction equation
[C:1]([O-:6])(=[O:5])[CH2:2][CH:3]=[CH2:4].[K+].[CH:8](Br)=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[C:10]1([CH:9]=[CH:8][CH:4]=[CH:3][CH2:2][C:1]([OH:6])=[O:5])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7667beta-BromostyreneHCID 23681240Potassium 3-butenoate

Product 1

HCID 537609956-Phenyl-3,5-hexadienoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

Proceeding as in Example 1, into a 100 cc flask were placed to react: 4.1 g of potassium 3-butenoate (3.3 10-2 mols), 6 g of styryl bromide, a cis-trans mixture, (3.3 10-2 mols), 2.9 g of Ni(PPh3)3 (3.3 10-2 mols) and 40 cc of ethyl alcohol. The mass was heated up to 105° C. under nitrogen atmosphere, for about 2 hours. Operating as in Example 1, there were obtained 2.2 g of 6-phenyl-3,5-hexadienoic acid, a mixture of isomers containing double cis and trans bonds.

Workup

  1. customProceeding as in Example 1, into a 100 cc flask were placed
  2. customto react

Sources & evidence

ORD record
ord-148829b496b1426d90c04c80d7ee5d7a
Source dataset
uspto-grants-1982_01
Patent number
US04309357

Reaction notes

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