Hydrochloric Acid → Undecanoic acid, butyl ester

HRID 978759Notes

Reaction equation

HRID 978759 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:2].[CH2:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].Cl>O1CCOCC1.[Pd](Cl)Cl>[CH3:8][CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:1]([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:2].[C:1]([O:3][CH2:4][CH2:5][CH2:6][CH3:7])(=[O:2])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11614Butyl FormateHCID 133811-Decene

Product 2

HCID 25404Undecanoic acid, butyl esterHCID 20203648HCID 20203648, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of palladium chloride [27 mg, 0.15 mmol] and CuCl2 [41 mg, 0.30 mmol] in dioxane (10 ml) was stirred under carbon monoxide for 5 minutes. Then n-butyl formate (4 ml), 1-decene [0.75 g, 5.35 mmol] and aqueous hydrochloric acid (0.1 ml) were added and CO/O2 (1:1) was bubbled through the solution at room temperature and atmospheric pressure for a period of 24 hours. Analysis of the product gave n-butyl 2-methyldecanoate and n-butyl undecanoate with respectively 87% and 13% selectivity with a 64% conversion of the formic acid ester.

Workup

  1. customCO/O2 (1:1) was bubbled through the solution at room temperature
  2. waitatmospheric pressure for a period of 24 hours

Sources & evidence

ORD record
ord-1488a602b15a400b923280f69ed446c4
Source dataset
uspto-grants-1987_05
Patent number
US04665213

Reaction notes

Loading…