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

HRID 589321

反応式

HRID 589321 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 21218Trioctylmethylammonium chloride触媒HCID 962Water溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0682b115e54c4959a645dc54984e67f5
出典データセット
uspto-grants-2016_01
特許番号
US09233115B2

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