ChemicalBook CAS DataBase List 3-oxo-2-pentylcyclopentaneacetic acid

3-oxo-2-pentylcyclopentaneacetic acid synthesis

13synthesis methods

Product Name:3-oxo-2-pentylcyclopentaneacetic acid
CAS Number:3572-64-3
Molecular formula:C12H20O3
Molecular Weight:212.29

24851-98-7 Synthesis

24851-98-7
388 suppliers
$6.00/10g

3572-64-3
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$43.00/100mg

Yield: 99%

Reaction Conditions:

Stage #1:methyl 3-oxo-2-pentylcyclopentaneacetate with sodium hydroxide in methanol at 20; for 24 h;
Stage #2: with hydrogenchloride in methanol;water; pH=~ 1

Steps:

1.1
Sodium hydroxide pellets (82.6g) were dissolved in methanol (425 ml) with stirring. This solution was added to a stirred solution of methyldihydrojasmonate (425g)(obtained from F. D. Copeland) in methanol (425 ml). The reaction mixture was stirred at room temperature for 24 hours. After this time TLC analysis (10:90 ethylacetate EtOAc):Hexane) confirmed that all starting material had been consumed. Aqueous 1M hydrochloric acid solution was added slowly until the pH of the reaction mixture was ~1. The aqueous/methanol solution was extracted with ethyl acetate (4 x 150 ml) and the combined organic extracts were dried (MgS04) and evaporated under vacuum to give the dihydrojasmonic acid as a pale yellow oil (397.0g,>99%). The structure was confirmed using 1H and 1³C NMR.

References:

BIOFUTURES PI LIMITED WO2005/102047, 2005, A1 Location in patent:Page/Page column 14