p-Toluenesulfonic acid → HCID 86694793, Verbindung

HRID 1410315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410315
[CH2:1]([C:7]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:19]2[CH:18]=[C:17]3[CH:20](O)[CH:21]([CH3:23])[CH2:22][C:16]3=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:25]([C:7]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:19]2[CH:18]=[C:17]3[CH:20]=[C:21]([CH3:23])[CH2:22][C:16]3=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 71089357HCID 71089357, Verbindung

Produkt 1

HCID 86694793HCID 86694793, VerbindungAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

In a 500 mL round flask, 9,9-dihexyl-2-methyl-1,2,3,9-tetrahydrocyclopenta[b]fluoren-1-ol (80 g, 197.7 mmol) and p-toluene sulfonic acid (0.2 g) were dissolved in 320 mL of toluene, and then water was completely removed under reflux with Dean-Stark. The resultant material was cooled to room temperature, and then an aqueous ammonium chloride solution (150 mL) and 200 mL of diethyl ether were injected thereto, followed by separation of the organic layer. The organic layer collected by extracting the residue with diethyl ether was dried over magnesium sulfate, followed by removal of volatile materials, and then purified by using silica gel column chromatography tube, to thereby obtain 74.0 g of 9,9-dihexyl-2-methyl-3,9-dihydrocyclopenta[b]fluorene (yield: 96.8%).

Aufarbeitung

  1. customwater was completely removed
  2. temperatureunder reflux with Dean-Stark
  3. customfollowed by separation of the organic layer
  4. customThe organic layer collected
  5. extractionby extracting the residue with diethyl ether
  6. dry with materialwas dried over magnesium sulfate
  7. customfollowed by removal of volatile materials
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-a775aa9b4bfb45a5aff2b6d87f7193d5
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921499B2

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