Ethyl 2-oxohexanoate

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Ethyl 2-oxohexanoate Basic information
Product Name:Ethyl 2-oxohexanoate
Synonyms:2-oxohexanoic acid ethyl ester;ethyl alpha-ketocaproate;Ethyl 2-oxohexanoate;2-Ketocaproic acid ethyl ester;2-Oxyhexanoic acid ethyl ester;2-ketoHexanoicacidethylester;Hexanoic acid, 2-oxo-, ethyl ester;Ethyl 2-oxohexanoate - [E12153]
CAS:5753-96-8
MF:C8H14O3
MW:158.2
EINECS:1308068-626-2
Product Categories:API
Mol File:5753-96-8.mol
Ethyl 2-oxohexanoate Structure
Ethyl 2-oxohexanoate Chemical Properties
Boiling point 96°C
density 0.981
Fp 81°C
storage temp. Sealed in dry,Room Temperature
AppearanceLight yellow to green yellowLiquid
Safety Information
HS Code 2918300090
MSDS Information
Ethyl 2-oxohexanoate Usage And Synthesis
Chemical PropertiesPale yellow liquid
Synthesis Reference(s)The Journal of Organic Chemistry, 29, p. 2080, 1964 DOI: 10.1021/jo01030a549
Synthesis
BUTYLZINC BROMIDE

92273-73-9

Ethyl chlorooxoacetate

4755-77-5

Ethyl 2-oxohexanoate

5753-96-8

General procedure for the synthesis of ethyl 2-oxohexanoate from n-butylzinc bromide and monoethyl oxalyl chloride: a stirred solution of copper iodide (2.29 g, 12 mmol) in anhydrous tetrahydrofuran was cooled to -25 °C and a tetrahydrofuran solution of 0.5 M n-butylzinc bromide (24 mL, 12 mmol) was added slowly dropwise. After addition, the reaction mixture was warmed to 0 °C and stirred at that temperature for 20 min, then cooled to -25 °C again. The reaction mixture was treated dropwise with monoethyl oxalyl chloride (1.37 g, 10 mmol). After stirring at -25 °C for 3 h, the reaction mixture was warmed to room temperature, the reaction was quenched with saturated aqueous ammonium chloride solution and the aqueous layer was extracted with ether. The combined organic phases were washed with brine, filtered, dried over anhydrous sodium sulfate and concentrated in vacuum. The crude product was purified by ISCO fast column chromatography using a pre-populated RediSep silica gel column (gradient elution, 0→20% ethyl acetate in hexane solution) to afford ethyl 2-oxohexanoate (0.60 g, 37%) as a colorless oil.1H NMR (400 MHz, CDCl3) δ 0.91-0.98 (3H, m), 1.34- 1.47 (5H, m), 1.58-1.76 (2H, m), 2.83 (1H, t, J = 7.3 Hz), 4.27-4.37 (2H, m).

References[1] Patent: US2008/90814, 2008, A1. Location in patent: Page/Page column 23-24
Ethyl 2-oxohexanoate Preparation Products And Raw materials
Raw materialsBUTYLZINC BROMIDE-->Ethyl chlorooxoacetate-->Tetrahydrofuran-->Copper(l) iodide
Tag:Ethyl 2-oxohexanoate(5753-96-8) Related Product Information
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