Carbon Dioxide → 2-(prop-2-yn-1-yl)pent-4-ynoic acid

HRID 2179478Notes

Reaction equation

HRID 2179478 reaction equation
[CH2:1]([C:4]([CH2:11][C:12]#[CH:13])(C(O)=O)[C:5]([OH:7])=[O:6])[C:2]#[CH:3].C(=O)=O>>[CH2:1]([CH:4]([CH2:11][C:12]#[CH:13])[C:5]([OH:7])=[O:6])[C:2]#[CH:3]

Participants

3

Reactant 2

HCID 280Carbon DioxideHCID 12686700HCID 12686700, compound

Product 1

HCID 136736532-(prop-2-yn-1-yl)pent-4-ynoic acidYield 79.9%

Procedure

The dipropargylmalonic acid (26 gm, 0.443 mol) was heated neat at 135 C until CO2 stopped evolving. It was then allowed to cool to an oil. The oil was distilled at 0.5 psi. The remaining oily residue in the distillation flask and solid were combined (15.7 gm, 79.9% yield) and was used as is in the next step.

Workup

  1. temperatureto cool to an oil
  2. distillationThe oil was distilled at 0.5 psi

Sources & evidence

ORD record
ord-31fdaff746bd4e6994316235bc8c7e91
Source dataset
uspto-grants-2015_06
Patent number
US09068013B2

Reaction notes

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