p-Toluenesulfonic acid → HCID 86694793, compound

HRID 2273376Notes

Reaction equation

HRID 2273376 reaction equation
[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]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 71089357HCID 71089357, compound

Product 1

HCID 86694793HCID 86694793, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-fca913f7bf624e55ac8d2519184108e2
Source dataset
uspto-grants-2015_09
Patent number
US09120884B2

Reaction notes

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