Carbon Tetrachloride → 9,9-Dichloro-9H-fluorene
Reaction equation
[CH:1]1[C:13]2C[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:14]([Cl:18])(Cl)(Cl)[Cl:15]>>[Cl:15][C:14]1([Cl:18])[C:4]2[CH:3]=[CH:2][CH:1]=[CH:13][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2Participants
Procedure
To the reactor which has been purged with nitrogen is charged a volume of carbon tetrachloride (400 mL) such that its level just comes to the bottom of the sixth stage. NaOH solution (the same solution used in Recycle run #1, 25 percent by weight, 6.14 moles, 245.6 g dry weight, 983 g solution weight, 774.0 mL) is then charged to the reactor, and fills all six of the stirred zones. The stirrer is started and its speed adjusted to 1500 rpm. Fluorene (0.185 moles, 30.75 g) dissolved in carbon tetrachloride (2.24 moles, 344.8 g, 225.35 mL) is fed into the catalyst saturator containing the catalyst solution using a metering pump at a rate of 5.5 mL/min. The product solution is collected at the overflow, washed and dried as in Part A. The total product solution collected in this fashion amounts to 1006 g which is evaporated to dryness on the rotary evaporation leaving 42.23 g of very light yellow crystals, 9,9-dichlorofluorene (97.1 percent of the theoretical yield of 43.49 g).
Workup
- customTo the reactor which has been purged with nitrogen
- additionis charged a volume of carbon tetrachloride (400 mL) such that its level
- dry with materialdry weight, 983 g solution weight, 774.0 mL)
- additionis then charged to the reactor
- additioncontaining the catalyst solution
- customThe product solution is collected at the overflow
- washwashed
- customdried as in Part A
- customThe total product solution collected in this fashion
- customis evaporated to dryness on the rotary evaporation
Sources & evidence
- ORD record
- ord-a42b61abdde2420f97a8a3298e2453e7
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05578737
Reaction notes
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