methyl 12-bromododecanoate synthesis

9synthesis methods

Product Name:methyl 12-bromododecanoate
CAS Number:26825-95-6
Molecular formula:C13H25BrO2
Molecular Weight:293.24

558-13-4 Synthesis

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Dodecanoic acid, 12-hydroxy-, Methyl ester

71655-36-2
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26825-95-6
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Yield: 2.65 g (90%)

Reaction Conditions:

with triphenylphosphine in toluene

Steps:

21.1 Example 21
(1) Methyl 12-hydroxydodecanoate (2.30 g, 10.0 mmol), triphenylphosphine (3.93 g, 1.5 eq), carbon tetrabromide (4.97 g, 1.5 eq) were stirred in toluene (10 ml) at room temperature for 3 hr. The reaction solution was filtered, followed by concentration to dryness. The residue was purified by column chromatography on silica gel (toluene-ethyl acetate (99: 1)) to give 2.65 g (90%) of methyl 12-bromododecanoate. ¹H-NMR (CDCl₃) δ: 1.20-1.35 (12H, m), 1.39-1.43 (2H, m), 1.56-1.63 (2H, m), 1.82-1.88 (2H, m), 2.30 (2H, t, J = 7.6 Hz), 3.41 (2H, t, J = 7.6 Hz), 3.73 (3H, s) IR (KBr): 1742 cm^-1EI-MS m/z: 293 (M⁺)

References:

Drug Delivery System Institute, Ltd.;MEIJI SEIKA KAISHA LTD.;Asahi Kasei Kogyo Kabushiki Kaisha EP953357, 1999, A1

67-56-1 Synthesis