Water → Undecanoic Acid

HRID 1656784Notes

Reaction equation

HRID 1656784 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]CCC.[OH2:30].[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>>[C:35]([OH:34])(=[O:30])[CH2:31][CH2:32][CH2:33][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 133811-Decene

Product 1

HCID 8180Undecanoic AcidYield 68%

Conditions

Temperature
50 °C

Procedure

The [PdCl2 /CuCl2 /CO] complex was freshly prepared as described above. To this catalyst (0.16 mmol) was added a solution of triphenylphosphine (0.13 g, 0.50 mmol). The mixture was transferred to an autoclave (Hastelloy B, 100-mL). A solution of 1-decene (1.12 g, 8.0 mmol), H2O (1 mL), and THF (15 mL) was then added via syringe. The autoclave was purged with CO (2×500 psig) and was then pressurized with CO (500 psig). The reactor was agitated at 50° C. overnight. GC analysis of an aliquote showed a 1:1 mixture of 2-methyldecanoic acid and n-undecanoic acid in 70% conversion. The reactor was cooled to room temperature and CO pressure was released. Standard workup yielded undecanoic acid (1.0 g, 68% yield) as an oil.

Workup

  1. customThe [PdCl2 /CuCl2 /CO] complex was freshly prepared
  2. customThe autoclave was purged with CO (2×500 psig)
  3. additiona 1:1 mixture of 2-methyldecanoic acid and n-undecanoic acid in 70% conversion
  4. temperatureThe reactor was cooled to room temperature

Sources & evidence

ORD record
ord-c9d695ffbb38498e9638d6025463c448
Source dataset
uspto-grants-1993_10
Patent number
US05254720

Reaction notes

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