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

HRID 589321

반응식

HRID 589321 반응식
[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]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 220445222-(Undec-10-en-1-yl)-1H-isoindole-1,3(2H)-dioneHCID 23665763Sodium Bisulfite

생성물 1

HCID 1362263910-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)decanoic acid수율 61%

시약·촉매·용매 3

HCID 21218Trioctylmethylammonium chloride촉매HCID 962Water용매HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0682b115e54c4959a645dc54984e67f5
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233115B2

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