Water → 4-Methyl-1,5-hexadien-1-yl pivalate

HRID 1979129

Reaction equation

HRID 1979129 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[C:6]([O:12][CH:13]=[CH2:14])(=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].O>CO.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[C:6]([O:12][CH:13]=[CH:14][CH2:4][CH:3]([CH3:5])[CH:2]=[CH2:1])(=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 6557IsopreneHCID 256591Vinyl pivalate

Product 1

HCID 545550354-Methyl-1,5-hexadien-1-yl pivalate

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

(Benzene)ruthenium dichloride dimer (14 mg, 0.056 mmol Ru), silver triflate (20 mg, 0.078 mmol) and 2,2-methylenebis(4-phenyl-2-oxazoline) (17.8 mg, 0.058 mmol) were dissolved in 2 ml of methanol. To the mixed solution were added isoprene (2 ml) and vinyl pivalate (1 ml) and the mixture was stirred under heat at 100° C. for 10 hours. The resulting product was poured into water and the separated organic layer was subjected to a GLC analysis. As a result, it was confirmed that a co-dimer was produced with the conversion rate being 72% and the ratio of an isomer being 4:1.

Workup

  1. customwas produced with the conversion rate

Sources & evidence

ORD record
ord-586fd727864b4946a264c95365a165aa
Source dataset
uspto-grants-2001_05
Patent number
US06239324B1

Linked notes

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