3-Butynoic acid

ChEBI: A monocarboxylic acid consisting of acetylene carrying a carboxymethyl group.

3-butynoic acid is a monocarboxylic acid consisting of acetylene carrying a carboxymethyl group. It is a monocarboxylic acid and a terminal acetylenic compound. It is a conjugate acid of a 3-butynoate.

After adding dropwise, 120 g of bromopropyne was added dropwise under the protection of nitrogen in a 1000-ml three-necked flask with 24 g of magnesium turnings and 300 ml of tetrahydrofuran as a solvent, and the reaction was carried out at room temperature for 60 minutes. The excess carbon dioxide was heated to 60 And the reaction mixture was poured into a saturated aqueous ammonium chloride solution cooled to 200 mg, extracted, separated and separated. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The organic layer was dried over anhydrous sodium sulfate The crude product of 3-butynoic acid was recrystallized from 50 ml of methyl t-butyl ether and filtered to obtain crystals. The crystals were dried to give 70 g of 3-butynoic acid as a pure product, Was 98.3percent.Preparation 1: Synthesis of 3-butynoic acidOH03-butynoic acid was prepared from the oxidation of 3-butyn-1-oI and following the reported procedure (Schmieder-van de Vondervoort, L. et a., P. L. SynIett2002, 2002, 0243). Water (45 mL) was added to a 150 mL single neck RBF fitted with a magnetic. stirrer bar. 65percent HNO3 (0.17 mL, 5 molpercent, 2.5 mmol), Na2Cr2O7 (0.15 g, I molpercent, 0.5 mmol) and NaIO4 (23.53 g, 2.2 eq., 110 mmol) were subsequently added to the RBF and the mixture was stirredvigorously on an ice bath for 15 mm. 3.78 mL of 3-butyn-1-ol (1 eq., 50 mmol) dissolved in45 mL of chilled water was added to this mixture slowly and the reaction mixture was left for18 — 24 hrs (ice bath was not removed to let the ice melt and temperature of reaction mixturerise slowly to rt). After this time, the product was extracted in diethyl ether (80 mL X 6). All ofthe fractions were combined and dried over anhydrous magnesium sulphate. The solventwas removed usinga rotary evaporator to give an orange/yellowish viscous liquid.Subsequent addition of dichloromethane and removal of solvent on a rotary evaporator (under vacuum) 4-5 times gave 3.20 g of an off white/yellowish solid (38 mmol, yield 76percent).1H NMR (400 MHz, CDCI3) 6 3.38 (d, 2H, J 2.7 Hz), 2, 25 (t, IH, J = 2.7 Hz); 13C NMR(400 MHz, CDCI3) 6 173.8, 74.8, 72.4, 25.6

Molecular Weight:84.07
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:84.021129366
Monoisotopic Mass:84.021129366
Topological Polar Surface Area:37.3
Heavy Atom Count:6
Complexity:95.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes