Acetic Acid → 10-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)decanoic acid

HRID 1037737

Reaktionsgleichung

[CH2:1]([N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]CC=C.[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(O)[O-].[Na+].[C:34]([OH:37])(=[O:36])[CH3:35]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CCCCCC.O>[O:22]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[N:12]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:35][C:34]([OH:37])=[O:36]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of 2-undec-10-enyl-1,3-dioxo-1,3-dihydroisoindole (2 g, 6.68 mmol) of Step 1 and Aliquat® 336 (0.2 g) in a mixture of hexane (20 ml) and acetic acid (6 ml) was added dropwise to a solution of potassium permanganate (2.76 g, 20 mmol) in water (28 ml) while cooling at 0° C. The reaction mixture was stirred at room temperature for 7 hours, then an aqueous solution of sodium bisulfite was added until disappearance of the purple colour. The mixture was then extracted with ethyl acetate and the organic phase was dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography eluting with 2:1 hexane:ethyl acetate mixture. The product was obtained as a white solid (1.29 g, 61% yield).

Aufarbeitung

extractionThe mixture was then extracted with ethyl acetate
dry with materialthe organic phase was dried over sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography
washeluting with 2:1 hexane

Quellen und Nachweise

ORD-Eintrag: ord-5c720a53c93d4c29b5a6944abfa211af
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08546608B2

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