p-Toluenesulfonic acid → HCID 123282959, compound

HRID 926680Notes

Reaction equation

HRID 926680 reaction equation
[C:1]([OH:6])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1>>[CH:10]1([CH:9]([O:5][C:1](=[O:6])[CH:2]=[CH:3][CH3:4])[CH3:8])[CH2:11][CH2:12][CH2:7][CH2:17]1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 637090Crotonic Acid

Product 1

HCID 123282959HCID 123282959, compound

Procedure

Cyclopentene reacted with carbon monoxide (CO) and hydrogen (H2) in the presence of a Wilkinson's catalyst to provide cyclopentanecarboxaldehyde, which then reacted with methylmagnesium chloride (MeMgCl) to provide 1-cyclopentylethanol, which further reacted with crotonic acid in the presence of p-toluenesulfonic acid (pTSA) to afford product but-2-enoic acid 1-cyclopentyl-ethyl ester.

Sources & evidence

ORD record
ord-ed878cb012d94833a19abe160e021f55
Source dataset
uspto-grants-2016_03
Patent number
US09289366B2

Reaction notes

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