| Identification | More | [Name]
4'-Methylvalerophenone | [CAS]
1671-77-8 | [Synonyms]
1-(4-Methylphenyl)-1-pentanone
4-Methyl-1-pentanoylbenzene
4'-Methylvalerophenone
1-(4-methylphenyl)pentan-1-one
1-(4-Methylphenyl)pentane-1-one | [EINECS(EC#)]
216-804-1 | [Molecular Formula]
C12H16O | [MDL Number]
MFCD00027237 | [Molecular Weight]
176.25 | [MOL File]
1671-77-8.mol |
| Hazard Information | Back Directory | [Uses]
4’-Methylvalerophenone is a Valerophenone derivative. Valerophenone (V091450) is an aromatic ketone that is often used as a tool in the study of various photochemical processes. Valerophenone is also an inhibitor of the enzyme carbonyl reductase. | [Synthesis]
The general procedure for the synthesis of 4-methylpentanone from the compound (CAS: 91763-35-8) is as follows: the oxidation reaction of 1-phenyl-1-pentanol (1a) was performed as a representative operation (see Table 2, entry 1): in a reaction flask fitted with a reflux condenser and a drying tube lined with calcium chloride, BMI-PF6 (85 mg, 0.30 mmol), 1- phenyl-1-pentanol (1a, 33 mg, 0.20 mmol), Cs2CO3 (33 mg, 0.10 mmol) and trifluoromethylbenzene (0.10 mL). The reaction mixture was stirred at 105 °C for 20 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and poured into water. The aqueous phase was extracted three times with ethyl acetate. The organic layers were combined, dried with anhydrous Na2SO4, filtered through a neutral alumina pad and concentrated under reduced pressure. Finally, purification by silica gel column chromatography using hexane/ethyl acetate (10:1, v/v) as eluent gave 1-phenyl-1-pentanone (2a, 28 mg, 0.17 mmol) in 86% yield. | [References]
[1] Angewandte Chemie - International Edition, 2003, vol. 42, # 41, p. 5063 - 5066
[2] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5392 - 5394 |
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