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73641-06-2

Octadecanoic acid, 16-methyl-, (-)- synthesis

1synthesis methods
56523-59-2 Synthesis
15-BROMOPENTADECANOIC ACID

56523-59-2
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$200.00/0.25g

sec-BuMgBr, Fandachem

671795-46-3
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Octadecanoic acid, 16-methyl-, (-)-

73641-06-2
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-

Yield:73641-06-2 95%

Reaction Conditions:

Stage #1: 15-bromo-pentadecanoic acid;sec-butylmagnesium bromidewith 18-crown-6 ether;triphenylphosphine;copper(I) bromide in tetrahydrofuran at 20;Inert atmosphere;
Stage #2: with sulfuric acid in tetrahydrofuran;water;Product distribution / selectivity;

Steps:

A2-1

Example A2-1 Preparation of 16-methyloctadecanoic acid [Show Image] To a four-necked 50 mL of flask equipped with a refluxing condenser tube, a 10 mL of dropping funnel, a magnetic stirrer and a temperature sensor, 15-bromopentadecanoic acid of 1.01g (3.14 mmol) and 18-crown-6 of 823.3 mg (1.0 eq) were added and dried under reduced pressure. Under argon atmosphere, copper bromide (I) of 13.3 mg (0.03 eq) and anhydrous tetrahydrofuran of 6 mL were added to dissolve the materials. At room temperature, sec-butyl magnesium bromide of 7.85 mL (2.5 eq, 1.0M tetrahydrofuran solution) was added dropwise thereto over thirty minutes. After stirring for one hour, 5 mL of 6N aqueous sulfuric acid solution was added and the extraction was carried out by using 10 mL of hexane . After washing twice with 10 mL ion exchange water, the mixture was dried over magnesium sulfate. After the filtration, the crude product (0.84 g) was obtained by concentration under reduced pressure. Gas chromatography (column : Ultra-2 manufactured by Agilent Technologies Inc., 30 m x 0.2 mm x 0.33 μm, DET 300°C, INJ 300°C, column temperature 100°C→ 300°C, 10°C/min) was carried out. As a result, the yield was 95%.

References:

EP2143705,2010,A1 Location in patent:Page/Page column 15

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