Chloride → HCID 11096896, compound

HRID 2425336Notes

Reaction equation

HRID 2425336 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].[Cl-]>CCCCCC.O.CN(C)C=O>[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

8

Reactant 4

HCID 312ChlorideHCID 6853FluoreneHCID 7850Allyl chlorideHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 11096896HCID 11096896, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 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. To the resultant mixture, 120 mL of dry N,N-dimethylformamide manufactured by Wako Pure Chemical Industries, Ltd. were added. While stirring the mixture at 50° C. under a nitrogen atmosphere, 5.86 mL of allyl chloride manufactured by Kanto Chemical Co., Inc. were added dropwise thereto over two hours. The mixture was stirred for 8 hours at 50° C., and 10.1 g of potassium tert-butoxide manufactured by Aldrich Chemical Company were added thereto, and then, 5.86 mL of ally chloride manufactured by Kanto Chemical Co., Inc. were added dropwise thereto over two hours. The mixture was stirred at 50° C. overnight. The reaction mixture was added to 900 mL of water, and 300 mL of hexane were added to the resultant mixture. The resultant organic layer was extracted with ether three times. The extract was washed with water four times, and was further washed with dilute hydrochloric acid and water, respectively. The washed extract was dried over anhydrous magnesium sulfate manufactured by Nacalai Tesque, Inc. The dried mixture was subjected to evaporation to remove the solvents contained therein. The obtained liquid was distilled in vacuo, thereby obtaining 12.8 g of 9,9-diallylfluorene as a yellow and oily fraction at 90° C. under a pressure of 4 mmHg.

Workup

  1. additionwere added
  2. additionwere added dropwise
  3. stirringThe mixture was stirred for 8 hours at 50° C.
  4. additionwere added
  5. additionwere added dropwise
  6. waitover two hours
  7. stirringThe mixture was stirred at 50° C. overnight
  8. extractionThe resultant organic layer was extracted with ether three times
  9. washThe extract was washed with water four times
  10. washwas further washed with dilute hydrochloric acid and water
  11. extractionThe washed extract
  12. dry with materialwas dried over anhydrous magnesium sulfate
  13. customThe dried mixture was subjected to evaporation
  14. customto remove the solvents
  15. distillationThe obtained liquid was distilled in vacuo

Sources & evidence

ORD record
ord-113f5483d6714ded9d3f1b5d246e5d9b
Source dataset
uspto-grants-2011_06
Patent number
US07964691B2

Reaction notes

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