Water → HCID 11096896, compound

HRID 2421458Notes

Reaction equation

HRID 2421458 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C[C:15]([CH3:18])([O-])[CH3:16].[K+].[CH2:20](Cl)[CH:21]=[CH2:22].O>CCCCCC>[CH2:16]([C:12]1([CH2:22][CH:21]=[CH2:20])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:15]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6853FluoreneHCID 7850Allyl chloride2×HCID 23665647Potassium tert-butoxide2×

Product 1

HCID 11096896HCID 11096896, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

There were put 10 g of fluorene manufactured by Wako Pure Chemical Industries, Ltd. and 10.1 g of potassium tert-butoxide manufactured by Aldrich Chemical Company in a 200 mL-round bottom flask, and 120 mL of dry N,N-dimethylformaide manufactured by Wako Pure Chemical Industries, Ltd. were added thereto. While stirring the resultant mixture in a nitrogen atmosphere at 50° C., 5.86 mL of allyl chloride manufactured by Kanto Chemical Co., Inc. were added dropwise thereto over 2 hours. The mixture was stirred at 50° C. for 8 hours. Additional 10.1 g of potassium tert-butoxide manufactured by Aldrich Chemical Company were added thereto, and then additional 5.86 mL of allyl chloride manufactured by Kanto Chemical Co., Inc. were added dropwise thereto over 2 hours. The mixture was stirred overnight at 50° C. The obtained reaction mixture was added to 900 mL of water, and then 300 mL of hexane were added thereto. The organic layer thereof was subjected to extraction with ether three times, and the extract was washed with water four times. The washed extract was further washed with diluted hydrochloric acid, and then with water in this order. The further washed extract was dried over anhydrous magnesium sulfate manufactured by Nacalai Tesque, Inc. The dried extract was subjected to removal of the solvent by distillation, and the resultant liquid was distilled in vacuo, thereby obtaining 12.8 g 9,9-diallylfluorene at 90° C. under 4 mmHg as yellow oil.

Workup

  1. additionwere added
  2. additionwere added dropwise
  3. additionwere added
  4. additionwere added dropwise
  5. waitover 2 hours
  6. stirringThe mixture was stirred overnight at 50° C
  7. customThe obtained reaction mixture
  8. extractionThe organic layer thereof was subjected to extraction with ether three times
  9. washthe extract was washed with water four times
  10. extractionThe washed extract
  11. washwas further washed with diluted hydrochloric acid
  12. washThe further washed
  13. extractionextract
  14. dry with materialwas dried over anhydrous magnesium sulfate
  15. extractionThe dried extract
  16. customwas subjected to removal of the solvent by distillation
  17. distillationthe resultant liquid was distilled in vacuo

Sources & evidence

ORD record
ord-0d599017312044fca17c5380fa682193
Source dataset
uspto-grants-2011_06
Patent number
US07956145B2

Reaction notes

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