ChemicalBook CAS DataBase List 2-HEXYNOIC ACID

2-HEXYNOIC ACID synthesis

4synthesis methods

Product Name:2-HEXYNOIC ACID
CAS Number:764-33-0
Molecular formula:C6H8O2
Molecular Weight:112.13

627-19-0 Synthesis

627-19-0
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124-38-9
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764-33-0
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$17.67/250mgs:

Yield: 91%

Reaction Conditions:

Stage #1:1-Pentyne;carbon dioxide with caesium carbonate in dimethyl sulfoxide at 60; under 760.051 Torr; for 24 h;Schlenk technique;
Stage #2: with hydrogenchloride in waterSchlenk technique;

Steps:

2.4. Catalytic tests
General procedure: The catalytic reaction was performed in a Schlenk reaction tube (10mL). Generally, a given amount of catalyst and dimethyl sulfoxide(DMSO) (3 mL) were loaded to the tube, and cesium carbonate (326 mg,1.0 mmol) was added under stirring. The atmosphere was exchange withCO2 and kept with a CO2 balloon, and meanwhile the tube was heatedwith an oil bath to 60 °C. Under rigorous stirring, a terminal alkyne (0.5mmol) was injected to initiate the reaction. After reacting for a giventime, the mixture was cool to room temperature and diluted with water(15 mL). After the catalyst was filtered off and washed with water, the filtrate was washed with dichloromethane (3 × 10 mL), acidified by 1 M HCl to pH≈1 and extracted with ethyl acetate (3 × 40 mL). The combinedorganic phase was washed by saturated NaCl solution and driedover anhydrous Na2SO4. The solvent was removed under vacuum toobtain the carboxylic acid product. For recycle tests, the used catalystobtained from the above procedures was further washed with acetone (3× 10 mL) to remove any unreacted alkyne and then heated at 60 °Cunder vacuum for 12 h.

References:

Bu, Ran;Zhang, Lin;Gao, Lu-Lu;Sun, Weng-Jie;Yang, Shuai-Liang;Gao, En-Qing [Molecular catalysis,2021,vol. 499,art. no. 111319]