Triethylamine → 9H-Fluoren-9-YL acrylate
Reaction equation
[OH:1][CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>C1C=CC=CC=1>[CH:13]1[C:14]2[CH:2]([O:1][C:22](=[O:25])[CH:23]=[CH2:24])[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 8 °C
Procedure
To a 250 mL round-bottomed flask was added 9-hydroxyfluorene (5 g, 27.4 mmol) and triethylamine (3.86 ml, 27.4 mmol) in benzene (150 mL) to give a colorless solution. The solution was cooled to 8° C. with an ice bath. Next, acryloyl chloride (2.229 mL, 27.4 mmol) was dissolved in 25 mL of benzene, placed in a dropping funnel, and added over 1 hour with vigorous stirring. The reaction formed a white precipitate. The ice bath was removed and the viscous sludge was stirred overnight at room temperature. The resulting cloudy white suspension was washed with 50 mL water, followed by 50 mL 5% NaOH solution, and 50 mL water. The benzene layer was collected and dried with MgSO4, filtered, and rotovapped to give the 9-fluorenylacrylate as a viscous beige oil which crystallized on cooling to 4° C. (4.73 g, 20.02 mmol, 73.0% yield).
Workup
- customto give a colorless solution
- customplaced in a dropping funnel
- additionadded over 1 hour with vigorous stirring
- customThe reaction formed a white precipitate
- customThe ice bath was removed
- washThe resulting cloudy white suspension was washed with 50 mL water
- customThe benzene layer was collected
- dry with materialdried with MgSO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-31841909e770484fbd5e10ccd5d213ec
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334026B2
Reaction notes
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