ChemicalBook CAS DataBase List 4-Chlorovalerophenone

4-Chlorovalerophenone synthesis

8synthesis methods

Product Name:4-Chlorovalerophenone
CAS Number:25017-08-7
Molecular formula:C11H13ClO
Molecular Weight:196.67

A mixture of 346 ml of chlorobenzene and 120 g of valeryl chloride is treated, at room temperature, in the course of 1 hour with portions of aluminium chloride and the mixture is at the same time heated to 70°. The mixture is stirred for a further hour at this temperature and then cooled to 25° and the dark red reaction mixture is poured on to 1,000 g of ice. Concentrated hydrochloric acid is added and the mixture is then extracted with ethyl acetate. The organic extract is washed with 2 N hydrochloric acid, filtered through a diatomaceous earth formulation (Hyflo) and washed with further 2 N hydrochloric acid, twice with water, with a 2 N aqueous solution of sodium carbonate and with water. It is dried over sodium sulphate and filtered and the filtrate is evaporated under reduced pressure. The residue is distilled; 4-Chlorovalerophenone is obtained at 155°-156°/14 mm Hg; the product crystallises and melts at 28°-30°.

29786-93-4 Synthesis

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Yield:25017-08-7 99 %Chromat.

Reaction Conditions:

Stage #1: 4-chloro-benzoyl chloridewith morpholine;diisobutylaluminium hydride in tetrahydrofuran;hexane at 0; for 0.166667 h;Inert atmosphere;
Stage #2: n-butyllithium in tetrahydrofuran;hexane at 0; for 0.166667 h;

Steps:

Partial alkylation of acid chlorides to corresponding ketones

General procedure: The following experimental procedure for the partial reduction of benzoyl chloride to 1-phenylpentanone is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.11 mL, 1.25 mmol) and 10 mL THF. After cooling to 0 °C, DIBALH (1.2 mL, 1.0 M in hexane, 1.2 mmol) was added dropwise and stirred for 3 h at same temperature. To the reaction mixture was slowly added benzoyl chloride (0.116 mL, 1.0 mmol) and stirred for 10 min. Then, n-BuLi (1.25 mL, 1.6 M in hexane, 2.0 mmol) was added and the mixture was stirred for 10 min again. The reaction was stopped by aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2 × 10 mL). The combined organic layers were dried over MgSO₄, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1-phenylpentanone (159 mg, 98%). All products in Table 3 were confirmed by comparison with NMR data reported in the literature.⁸

References:

Park, Jae Kyo;Shin, Won Kyu;An, Duk Keun [Tetrahedron Letters,2013,vol. 54,# 24,p. 3199 - 3203]

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