p-Toluenesulfonic acid → HCID 15333570, compound

HRID 1451559Notes

Reaction equation

HRID 1451559 reaction equation
[C:1]([C:3]1([OH:16])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)#[CH:2].[C:17]1(O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[O:16]1[C:3]2([C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]3[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:1]=[CH:2][C:24]2[CH:23]=[CH:22][C:21]3[C:26]([C:25]1=2)=[CH:17][CH:18]=[CH:19][CH:20]=3

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 70051-NaphtholHCID 14798Sodium HydroxideHCID 5187719-Ethynyl-9-fluorenol

Product 1

HCID 15333570HCID 15333570, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.09 g of 9-ethynyl-9-fluorenol (15 mmoles) and 2.49 g of 1-naphthol (17.25 mmoles) were dissolved under reflux in 30 ml of anhydrous toluene in an inert atmosphere. 0.03 g of PTSA was then added. The reaction mixture was refluxed in an inert atmosphere for 2 hours 30 minutes. On returning to room temperature, the mixture was poured onto an aqueous 10% caustic soda solution. After decanting, the aqueous phase was continuously extracted with dichloromethane. The organic phases were combined and dried over magnesium sulphate. The solvent was removed under reduced pressure. The compound was precipitated out with hexane then recrystallised from toluene.

Workup

  1. temperatureThe reaction mixture was refluxed in an inert atmosphere for 2 hours 30 minutes
  2. customOn returning to room temperature
  3. customAfter decanting
  4. extractionthe aqueous phase was continuously extracted with dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was removed under reduced pressure
  7. customThe compound was precipitated out with hexane
  8. customthen recrystallised from toluene

Sources & evidence

ORD record
ord-d7fe85af3ca54b73b2d76efcb984329f
Source dataset
uspto-grants-1997_02
Patent number
US05604280

Reaction notes

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