2-(Hex-5-ynyl)malonic acid → 7-Octynoic acid

HRID 1197348Notes

Reaction equation

HRID 1197348 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

HCID 193734072-(Hex-5-ynyl)malonic acid

Product 1

HCID 53127007-Octynoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. temperaturerefluxed, under nitrogen, for 6 hours
  2. customThe solvent was removed in vacuo
  3. addition5% Aqueous hydrochloric acid was added
  4. extractionthe aqueous mixture was extracted with diethyl ether
  5. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  6. 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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