Acetone → HCID 11604403, compound

HRID 1748704Notes

Reaction equation

HRID 1748704 reaction equation
[CH:1]1[C:13]2[C:12]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:28](Br)[CH:29]=[CH2:30].C([O-])([O-])=O.[K+].[K+].[CH3:38][C:39]([CH3:41])=O>>[CH2:28]([O:27][C:24]1[CH:23]=[CH:22][C:21]([C:12]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:41][CH:39]=[CH2:38])=[CH:16][CH:15]=3)[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:26][CH:25]=1)[CH:29]=[CH2:30]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 767169,9-Bis(4-hydroxyphenyl)fluorene

Product 1

HCID 11604403HCID 11604403, compound

Procedure

Into a 1,000 ml two-necked flask equipped with a refluxing condenser, 10.0 g of 4,4′-(9H-fluorene-9,9-diyl)diphenol (Sigma-Aldrich), 6.17 ml of allyl bromide (Sigma-Aldrich), 23.68 g of K2CO3, and 500 ml of acetone were charged and mixed at room temperature. Then, the temperature was set to 80° C., and the homogeneous mixture thus obtained was refluxed overnight. After finishing the reaction, the reaction mixture was cooled to room temperature and was filtered using Celite. The solvent was evaporated to obtain a coarse product. A target product was extracted from the coarse product using ethyl acetate, washed three times using water, and dried using MgSO4. MgSO4 was filtered off, and solvents were removed by using an evaporator to obtain an intermediate product (11), 9,9-bis(4-(allyloxy)phenyl)-9H-fluorene. The reaction scheme in the 1st step and the NMR data of the intermediate product (11) are as follows.

Workup

  1. customInto a 1,000 ml two-necked flask equipped with a refluxing condenser
  2. additionmixed at room temperature
  3. customwas set to 80° C.
  4. customthe homogeneous mixture thus obtained
  5. temperaturewas refluxed overnight
  6. customthe reaction
  7. filtrationwas filtered
  8. customThe solvent was evaporated
  9. customto obtain a coarse product
  10. extractionA target product was extracted from the coarse product
  11. washwashed three times
  12. customdried
  13. filtrationMgSO4 was filtered off
  14. customsolvents were removed
  15. customan evaporator

Sources & evidence

ORD record
ord-cc2e116d9a7c4717af892258d7aa71b8
Source dataset
uspto-grants-2015_10
Patent number
US09150686B2

Reaction notes

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