Hydrochloric Acid → 9-Ethynyl-9-fluorenol

HRID 2294275Notes

Reaction equation

HRID 2294275 reaction equation
[CH:1]1[C:13]2[C:12](=[O:14])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:15]1COC[CH2:16]1.[C-]#[C-].[Na+].[Na+].Cl>C1(C)C(C)=CC=CC=1>[C:15]([C:12]1([OH:14])[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)#[CH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10241FluorenoneHCID 178463197HCID 178463197, compound

Product 1

HCID 5187719-Ethynyl-9-fluorenol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

9 g (0.05 mol) of 9-fluorenone and 100 ml of anhydrous THF are charged into a dry flask of 250 ml. To the resulting solution a suspension of sodium acetylide [17.8 g (0.0525 mol) in mineral oil/xylene, 18% by weight based on the suspension; solid purity 95%] is added under nitrogen, by means of a syringe. The resulting suspension is kept overnight under nitrogen and with stirring before being poured into 75 ml of 10% HCl. The phases are separated and the aqueous phase is extracted twice with 100 ml of ethyl ether. The organic extracts are combined and thoroughly dried over sodium sulfate. By eliminating the solvent, 10.1 g of product is obtained, which is used without any further purification.

Workup

  1. additionsolid purity 95%] is added under nitrogen, by means of a syringe
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with 100 ml of ethyl ether
  4. dry with materialthoroughly dried over sodium sulfate

Sources & evidence

ORD record
ord-c5d223da2d444ae0a8da41efee7ae32b
Source dataset
uspto-grants-1997_11
Patent number
US05688846

Reaction notes

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