2-(Hex-5-ynyl)malonic acid → 7-Octynoic acid
Reaction equation
[CH2:1]([CH:7](C(O)=O)[C:8]([OH:10])=[O:9])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]>C(#N)C>[C:8]([OH:10])(=[O:9])[CH2:7][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(hex-5-ynyl)malonic acid (2.2 g) and cuprous oxide (60 mg) in dry acetonitrile (40 ml) was stirred and refluxed, under nitrogen, for 6 hours. The solvent was removed in vacuo. 5% Aqueous hydrochloric acid was added and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. Oct-7-ynoic acid was obtained as an oil (1.5 g) and was used without further purification.
Workup
- temperaturerefluxed, under nitrogen, for 6 hours
- customThe solvent was removed in vacuo
- addition5% Aqueous hydrochloric acid was added
- extractionthe aqueous mixture was extracted with diethyl ether
- dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-be8fb9c6dfd74b03bf3a33971a125ced
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05116862
Reaction notes
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