Methanesulfonic Acid → 1-Nonanol

HRID 1637051Notes

Reaction equation

HRID 1637051 reaction equation
[C:1]1([O:7]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O)(=O)=O.C(O[CH2:17][CH2:18][CH2:19]C)=O.C=CCCCCCC.C(O)#CCCCCC(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:17][CH2:18][CH3:19]

Participants

8

Reactant 5

HCID 6395Methanesulfonic AcidHCID 7519AnisoleHCID 81251-OcteneHCID 11614Butyl FormateHCID 20565036HCID 20565036, compound

Product 1

HCID 89141-Nonanol

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A 500 mL autoclave was charged with 0.76 mmol palladium (II)acetate, 1.07 mmol of a mixture of 1.2-bis(9-phosphabicyclononyl)ethane, 20.2 mL of anisole (as solvent), 0.45 mL methanesulfonic acid (MSA), 4.80 mL water, 7.91 mL butyl formate (as promoter), and 156 mL octene, 83 ml isononynol. The autoclave was flushed with an equimolar mixture of carbon monoxide and hydrogen pressurized to a total pressure of 50 bar. The autoclave was then sealed and the mixture was heated to 110° C. The reaction was continued for 8 hours and subsequently the reaction mixture was cooled to room temperature and the pressure released. 163 g of nonyl alcohol product was produced (94% conversion of starting material). The reaction rate was about 0.36 hr-1. There was no noticeable paraffin make. This example illustrates that the use of a formic acid derivative as a promoter results in high conversion/high selectivity reactions with excellent reaction rates.

Workup

  1. customThe autoclave was flushed with an equimolar mixture of carbon monoxide and hydrogen
  2. customThe autoclave was then sealed
  3. temperaturesubsequently the reaction mixture was cooled to room temperature

Sources & evidence

ORD record
ord-a5bcf6ce04ac45bf926811278eeec38c
Source dataset
uspto-grants-2000_03
Patent number
US06037506

Reaction notes

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