ChemicalBook CAS DataBase List Propiolic acid, (p-chlorophenyl)- (8CI)

Propiolic acid, (p-chlorophenyl)- (8CI) synthesis

12synthesis methods

Product Name:Propiolic acid, (p-chlorophenyl)- (8CI)
CAS Number:3240-10-6
Molecular formula:C9H5ClO2
Molecular Weight:180.59

873-73-4 Synthesis

873-73-4
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$5.00/100mg

124-38-9
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$175.00/23402

3240-10-6
53 suppliers
$52.00/100mg

Yield:3240-10-6 97%

Reaction Conditions:

Stage #1:4-n-chlorophenylacetylene;carbon dioxide with diethoxymethylane;potassium tert-butylate at 40; for 2 h;Schlenk technique;
Stage #2: with hydrogenchloride in waterSchlenk technique;

Steps:

2.2 General procedure for silylation/carboxylationtandem reaction and characterization data
General procedure: The terminal alkyne (1.0 mmol) was added to a mixtureof HSi(OEt)2Me (5.0 mmol) and KOtBu (1.5 mmol) in a10 mL Schlenk tube with a magnetic stirrer. The Schlenktube was evacuated and back-filled with CO2 for 3 times.After a CO2 ballon was connected, the reactor was moved toa water bath of 40 °C. After being stirred for 2 h, the reactionmixture was diluted with water (30 mL), and was extractedwith CH2Cl2 (3×10 mL). The aqueous layer was acidifiedwith aqueous HCl (6 M) and then extracted with diethylether (5×20 mL). The combined organic extracts were driedover Na2SO4 and concentrated under vacuum to give the purepropiolic acid (such as compound 3-phenylpropiolic acid(3a): 98%).

References:

Yu, Bo;Yang, Peng;Gao, Xiang;Yang, Zhenzhen;Zhao, Yanfei;Zhang, Hongye;Liu, Zhimin [Science China Chemistry,2018,vol. 61,# 4,p. 449 - 456]

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