ChemicalBook CAS DataBase List PROPYNAL

PROPYNAL synthesis

6synthesis methods

Product Name:PROPYNAL
CAS Number:624-67-9
Molecular formula:C3H2O
Molecular Weight:54.05

Propynal is most simply synthesized by oxidation of Propargyl Alcohol.^1,2

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624-67-9
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Yield:624-67-9 90%

Reaction Conditions:

with chromium(VI) oxide;sulfuric acid in water;butanone at 20 - 25; under 760.051 Torr; for 1 h;

Steps:

1.A.6.1 A.6.1) Preparation of N-(4-methoxyphenyl)-prop-2-yn-1-imine
N-(4-methoxyphenyl)-prop-2-yn-1-imine is obtained in two steps. First, 2-propynal is obtained from 2-propyn-l-ol as described in Veliev et al., 1980, Synthesis 6, 461. 2-propyn-l -ol is dissolved in 2-butanone (C₂H₅COCH₃) and oxidized by an aqueous solution of chromium trioxide (Cr0₃) and sulfuric acid (H₂S0₄) at ambient temperature and atmospheric pressure. A solution of chromium trioxide (60 g) in sulfuric acid (40 ml) and water (120 ml) is added dropwise with stirring over 1 hour to a solution of 2-propyn-l-ol (35.88 g, 37.26 ml, 640 mmol) in 2-butanone (100 ml). The temperature is maintained at 20-25°C by cooling. The reaction mixture is stirred for 4 hours and diluted with water (30 ml). The organic layer is separated. The aqueous layer is extracted with diethyl ether (Et₂0, 120 ml). The combined organic layers are dried over anhydrous magnesium sulfate (MgS0₄). The solvents are removed in vacuo. Distillation of the residual liquid gives 2-propynal (31.13 g, 34.98 ml, 576 mmol, 90%).

References:

VITA API;ETAT FRANÇAIS REPRÉSENTÉ PAR LE DIRECTEUR CENTRAL DU SERVICE DE SANTÉ DES ARMÉES;UNIVERSITÉ D'AIX-MARSEILLE;CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - CNRS -;SIMON, Philippe Yves-Rémy;OREAL, Henri;AUDRAN, Gérard;SCHULZ, Marvin;JOLY, Jean-Patrick;SIRI, Didier;SIRI, Anouk WO2018/115497, 2018, A1 Location in patent:Page/Page column 53; 54; 55

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107-19-7
0 suppliers
$12.00/25g

624-67-9
60 suppliers
$120.00/500mg