ChemicalBook CAS DataBase List 4-PENTYNOIC ACID

4-PENTYNOIC ACID synthesis

11synthesis methods

Product Name:4-PENTYNOIC ACID
CAS Number:6089-09-4
Molecular formula:C5H6O2
Molecular Weight:98.1

5390-04-5

6089-09-4

General procedure for the synthesis of 4-pentynoic acid from 4-pentyn-1-ol: 4-pentyn-1-ol (1 mL, 10.7 mmol) was dissolved in acetone and the solution was cooled to 0 °C. Jones' reagent was slowly added dropwise under vigorous stirring until the reaction mixture remained orange in color. Subsequently, the reaction mixture was allowed to warm up to room temperature and Jones reagent was continued to be added dropwise to maintain the orange color. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, water was added and extracted several times with ether (Et2O). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure to give the crude product. Purification by rapid chromatography on silica gel (eluent: hexane/ether=8:2) gave the colorless oily product 4-pentynoic acid in 82% yield.1H NMR (400MHz, CDCl3) δ: 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm.

5390-04-5
297 suppliers
$13.00/1g

6089-09-4
173 suppliers
$11.00/1g

Yield:6089-09-4 82%

Reaction Conditions:

with Jones reagent in acetone at 0 - 20; for 1 h;

Steps:

5 pent-4-ynoic acid (30d)
23d (lmL, 10.7 mmol) was dissolved in Acetone and cooled to 0°C. Jones reagent was added dropwise to the solution, under vigorous stirring, until the reaction mixture remained orange. The mixture was allowed to reach r.t., and more Jones reagent wasadded to maintain the orange colour. The reaction mixture was stirred at r.t. for lh, then water was added, and was extracted with Et20 several times, washed with Brine and dried over anhydrous Na2504. The solvent was removed at reduced pressure and the resulting oil purified by flash chromatography on silica gel (Hexane/Et20 8:2). Yield 82%, colourless oil. 1HNMR (400 MHz CDC13-d): ? 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm.

References:

AZIENDA OSPEDALIERA UNIVERSITARIA SENESE;MEYERHANS, Andreas;MARTINEZ DE LA SIERRA, Miguel-Angel;BRAI, Annalaura;FAZI, Roberta;TINTORI, Cristina;BOTTA, Maurizio;ARAQUE, José-Esté;MARTINEZ, Javier WO2016/128541, 2016, A1 Location in patent:Page/Page column 53

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