Methanesulfonic Acid → HCID 566761, compound

HRID 1911985Notes

Reaction equation

HRID 1911985 reaction equation
[C:1]([O:20][CH3:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CS(O)(=O)=O>CO.[Pd].C(P(CC1C=CC=CC=1CP(C(C)(C)C)C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:21][O:20][C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:3][CH2:2][C:1]([O:20][CH3:21])=[O:19])=[O:19]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 5364509Methyl Oleate

Product 1

HCID 566761HCID 566761, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 86675545HCID 86675545, compoundCatalystHCID 887MethanolSolvent

Procedure

210 ml of crude methyl oleate are reacted with 2.4 mol % of catalyst, in this example Pd/bis(di-tert-butylphosphinomethyl)benzene, in 770 ml of methanol and in the presence of 45 mol % of methanesulfonic acid at a temperature of 80° C. and a CO partial pressure of 30 000 hPa in a reaction time of 22 hours with constant stirring to give the alpha,omega-dicarboxylic diester, here 1,19-nonadecanedicarboxylic dimethyl ester. The catalyst was preformed in the same way as under example 1. The crude diester is purified as described under example 1. The yield is 76%, based on methyl oleate.

Sources & evidence

ORD record
ord-1c8550663f9045aab5aa0f59df4c1567
Source dataset
uspto-grants-2013_12
Patent number
US08604227B2

Reaction notes

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