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

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

Reactant 2

HCID 280Carbon Dioxide

HCID 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

temperatureto cool to an oil
distillationThe oil was distilled at 0.5 psi

Sources & evidence

ORD record: ord-5d7af7299a5840a8bc3d6ff4021a1a62
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940690B2

Reaction notes

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