Methanol → Methyl isobutyrate

HRID 65140

Reaction equation

HRID 65140 reaction equation
F[C:2](F)(F)[C:3]1[CH:8]=CC=C[C:4]=1P([C:16]1[CH:21]=CC=CC=1)C1C=CC=CC=1.C[OH:25].[O:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>[Pd](Cl)Cl>[C:4]([O:26][CH3:27])(=[O:25])[CH:3]([CH3:8])[CH3:2].[C:30]([O:29][CH3:28])(=[O:25])[CH2:31][CH2:21][CH3:16]

Participants

6

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 303893Diphenyl[2-(trifluoromethyl)phenyl]phosphane

Product 2

HCID 11039Methyl isobutyrateHCID 12180Methyl butyrate

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
120 °C

Procedure

The autoclave was charged with 0.3 gms of palladium chloride, 5 gms o-trifluoromethylphenyldiphenylphosphine, 10 mls of methanol and 50 ml of p-dioxane. After flushing with nitrogen, the autoclave was pressurized with carbon monoxide to 800 psig and heated to 120 degrees C. with stirring. 10 gms of liquid propylene was added and the reaction continued at 120° C. and 100 psig for 3 hours. The autoclave was then cooled and the reaction fluid analyzed by gas chromatography. A methyl isobutyrate:methyl n-butyrate ratio of 7.1:1 was obtained.

Workup

  1. customAfter flushing with nitrogen
  2. addition10 gms of liquid propylene was added
  3. customcontinued at 120° C.
  4. temperatureThe autoclave was then cooled

Sources & evidence

ORD record
ord-e5490df9d8cf467daca53ea437840a1c
Source dataset
uspto-grants-1986_09
Patent number
US04612390

Linked notes

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