Fluorene → 9,9-dihexylfluorene
Reaction equation
C1C2CC3C(=CC=CC=3)C=2C=CC=1.Cl[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[Cl-].[C:22]([C:31]([NH3+])([C:41](=O)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:32](=O)[CH2:33][CH2:34][CH2:35]CCCC)(=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]CC.[OH-].[Na+]>>[CH2:15]([C:31]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:48][C:47]=2[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]Participants
Conditions
- Temperature
- 50 °C
Procedure
A 250 ml flask was equipped with an electric stirrer, thermowell, and nitrogen pad. It was loaded at room temperature with 24.9 g (0.15 moles) fluorene, 39.5 g (0.327 moles) chlorohexane, 2.9 g of tricaprylylmethylammonium chloride (0.007 moles), and 180 g (2.25 moles) 50% NaOH. No exotherm is observed. It was then heated at 50° C. until reaching 99+% conversion. The reaction took approximately 12 hours. While maintaining at 50° C., the liquid phases were separated (the solid NaCl remained suspended in the top organic phase). The organic phase was extracted with 1×50 ml water followed by 1×25 ml 3.5% HCl (acid wash caused color change from dark to orange). The resulting organic phase weighed 55.8 g and had an area percentage GC analysis for dialkylated product in the 90's. The crude product was forwarded directly to the bromination reaction step. Based on the accountability in the bromination, the yield of the PTC alkylation was 92+%.
Workup
- customA 250 ml flask was equipped with an electric stirrer
- temperatureWhile maintaining at 50° C.
- customthe liquid phases were separated (the solid NaCl
- extractionThe organic phase was extracted with 1×50 ml water
- customThe crude product was forwarded directly to the bromination reaction step
Sources & evidence
- ORD record
- ord-dcd43e5322124956a11af51c3e2e849f
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07102042B2
Reaction notes
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