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

HRID 1776450Notes

Reaction equation

HRID 1776450 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-06bb52966caa440bb7db883f19e241cb
Source dataset
uspto-grants-2016_02
Patent number
US09265838B2

Reaction notes

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