4'-Methylvalerophenone synthesis
- Product Name:4'-Methylvalerophenone
- CAS Number:1671-77-8
- Molecular formula:C12H16O
- Molecular Weight:176.25
Yield:1671-77-8 94 %Chromat.
Reaction Conditions:
Stage #1: 4-methyl-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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