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

HRID 1354009

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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). M.p. 58–60° C.

Workup

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

Sources & evidence

ORD record: ord-fa51d15a78e54c8aae2ef4e92746a5d9
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223745B2

Linked notes

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