Water → HCID 86237345, compound

HRID 630646Notes

Reaction equation

HRID 630646 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+].[I-].[K+].O>CS(C)=O>[CH2:2]([C:7]1([CH2:7][CH2:6][CH2:14][CH3:13])[C:6]2[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:1][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 699082-Acetylfluorene

Product 1

HCID 86237345HCID 86237345, compoundYield 181.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
15 °C

Procedure

15.9 g of 2-acetylfluorene (11) (76.4 mmol), 18.9 g of potassium hydroxide (0.27 mol, purity: 80%), and 1.26 g of potassium iodide (7.6 mmol) were dissolved in 350 ml of anhydrous dimethylsulfoxide under nitrogen atmosphere, and a reaction temperature was maintained at 15° C. Then, 33 ml of n-bromobutane (0.3 mol) was slowly added thereto for 2 hours, followed by stirring at 15° C. for 1 hour. Thereafter 200 ml of distilled water was added to the reaction mixture and stirred for about 30 minutes, a product was extracted with 300 ml of dichloromethane, and the extracted organic layer was washed with 100 ml of distilled water three times. Then, the recovered organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure. The obtained product was purified using a silica gel column chromatography (developing solvent: dichloromethane:n-hexane=15:1), thereby obtaining 22.2 g of 1-(9,9-di-n-butylfluorene-2-yl)-ethanone (12) (90.8%) as a light yellow liquid.

Workup

  1. stirringstirred for about 30 minutes
  2. extractiona product was extracted with 300 ml of dichloromethane
  3. washthe extracted organic layer was washed with 100 ml of distilled water three times
  4. dry with materialThen, the recovered organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained product was purified

Sources & evidence

ORD record
ord-56f62b04df0c474884c03f8fe2fdf2bd
Source dataset
uspto-grants-2016_04
Patent number
US09316906B2

Reaction notes

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