ChemicalBook CAS DataBase List ACETIC ACID 3-BUTEN-2-YL ESTER

ACETIC ACID 3-BUTEN-2-YL ESTER synthesis

14synthesis methods

Product Name:ACETIC ACID 3-BUTEN-2-YL ESTER
CAS Number:6737-11-7
Molecular formula:C6H10O2
Molecular Weight:114.14

107-01-7
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64-19-7 Synthesis

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6737-11-7
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Yield:-

Reaction Conditions:

with oxygen;sodium acetate;palladium dichloride in N,N-dimethyl acetamide at 80; under 4500.45 Torr; for 4 h;

Steps:

1
Example 1Palladium chloride (62 mg, 0.35 mmol), sodium acetate (410 mg, 5 mmol), acetic acid (3.1 g (3 ml), 50 mmol), and dimethylacetamide (DMA, 5 ml) were charged in a pressure vessel. The pressure inside the vessel was reduced, and 2-butene (450 mg, 8 mmol) was added thereto. Then, the pressure inside the vessel was raised to 0.6 MPa by feeding oxygen gas thereto, and an esterification reaction was conducted at 80° C. for 4 hours.After completion of the reaction, the product was analyzed by using a gas chromatograph equipped with an FID detector (“GC-2014” manufactured by Shimadzu Corporation, column: KOCL 3 m). As a result, it was found that an acetoxyl group (AcO-) was bonded to a carbon atom in the CC bond of 2-butene or a carbon atom at an allylic position thereof, so that 2-butene-1-acetate and 3-butene-2-acetate were formed. Accordingly, 2-butene was presumably esterified by oxidatively bonding a carboxyl group as shown in the following reaction formula (I): In addition, Table 1 shows the conversion of 2-butene, the total yield of 2-butene-1-acetate and 3-butene-2-acetate based on the amount of 2-butene charged, and the isomer ratio between 2-butene-1-acetate and 3-butene-2-acetate.

References:

Osaka University;JX NIPPON OIL & ENERGY CORPORATION US2012/316360, 2012, A1 Location in patent:Page/Page column 7-9

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