ChemicalBook CAS DataBase List Nabumetone

Nabumetone synthesis

7synthesis methods

Product Name:Nabumetone
CAS Number:42924-53-8
Molecular formula:C15H16O2
Molecular Weight:228.29

73356-31-7 Synthesis

3-Buten-2-one, 4-hydroxy-4-(6-methoxy-2-naphthalenyl)-

73356-31-7
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42924-53-8
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Yield:42924-53-8 93%

Reaction Conditions:

palladium on charcoal catalyst in acetic acid

Steps:

3 Preparation of 4-(6'-methoxy-2'-naphthyl)butan-2-one
EXAMPLE 3 Preparation of 4-(6'-methoxy-2'-naphthyl)butan-2-one A solution of 4-(6'-methoxy-2'-naphthyl)-4-hydroxy-but-3-en-2-one (0.5 g, 0.00208 mole) in glacial acetic acid (50 ml) [effected by warming] was shaken in an atmosphere of hydrogen over 10% palladium on charcoal catalyst (0.05 g) at room temperature and atmospheric pressure until hydrogen uptake had ceased (approximately 2 hours). The catalyst was then removed by filtration and the filtrate concentrated in vacuo. The remaining brown oil was dissolved in ether and this solution washed with sodium bicarbonate solution, then water and dried (MgSO₄). Evaporation of solvent gave a pale yellow oil (0.47 g, 93%) which solidified on standing at room temperature to an off-white solid.

References:

Beecham Group Limited US4221741, 1980, A

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127053-22-9 Synthesis