ChemicalBook CAS DataBase List Cyclopropanecarboxylic acid

Cyclopropanecarboxylic acid synthesis

8synthesis methods

Product Name:Cyclopropanecarboxylic acid
CAS Number:1759-53-1
Molecular formula:C4H6O2
Molecular Weight:86.09

Cyclopropanecarboxylic acid has been prepared by the hydrolysis of cyclopropyl cyanide, although it is unnecessary to isolate the nitrile; by heating cyclopropanedicarboxylic acid; and by the action of alkali on ethyl γ-chlorobutyrate.7 The last two methods do not appear to be of practical importance. The oxidation of cyclopropyl methyl ketone with sodium hypobromite is reported to be an excellent preparative method for this acid.
Org. Synth. 1944, 24, 36
DOI: 10.15227/orgsyn.024.0036

1-cyclopropyl-4,4,4-trifluoro-1,3-butanedione

30923-69-4
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1759-53-1
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Yield:1759-53-1 98%

Reaction Conditions:

with oxygen;sodium hydrogencarbonate in acetonitrile; for 4 h;Molecular sieve;Irradiation;

Steps:

Representative procedure for oxidization of 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione (1n) to thiophene-2-carboxylic acid (2n) in 1.0 mmol scale under blue LED irradiation with molecular oxygen

General procedure: Photoredox catalyst [Ru(bpy)₃]Cl₂·6H₂O (6.4mg, 0.01 mmol) was added to a stirred suspension of 2 mL CH₃CN, β-diketone 1n (222mg, 1.0 mmol), 4? molecular sieve (200 mg) and NaHCO₃(84 mg, 1.0 mmol), the mixture was stirred under irradiation of 20W blue LED and charged with oxygen balloon for 4h unless otherwise noticed, after completion of the reaction, the resulted suspension was acidified with 1% HCl before filtered through celite, the filtrate was concentrated before purified through silica gel chromatography (gradient elution with hexanes/ethyl acetate from 3/1 to 2/1) to yield the carboxylic acid 2n ⁹ ( 126mg, 0.99 mmol, 99%) as white solid.(M. p = 125-129 ^oC) ¹H NMR (DMSO-d₆, 400 MHz, ppm) δ 13.06 (s, br, 1H), 7.88 (d, 1H, J = 4.8 Hz), 7.74 (d, 1H, J = 3.8 Hz); ¹³C NMR (DMSO-d₆, 100 MHz, ppm) δ 163.4, 135.2, 133.8, 133.7, 128.7.

References:

Wang, Xiao-Yan;Shang, Zhen-Peng;Zha, Gao-Feng;Chen, Xiao-Qing;Bukhari, Syed Nasir Abbas;Qin, Hua-Li [Tetrahedron Letters,2016,vol. 57,# 50,p. 5628 - 5631] Location in patent:supporting information