Benzene, 1-(chloromethyl)-2,3,4,5,6-pentamethyl- → 1,2,3,4,5-Pentamethylcyclopentadiene
Reaction equation
CC1[C:7]([CH2:8]Cl)=[C:6]([CH3:10])[C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[CH3:13]>C1COCC1>[CH3:13][CH:3]1[C:4]([CH3:12])=[C:5]([CH3:11])[C:6]([CH3:10])=[C:7]1[CH3:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A 250 ml roundbottom flask equipped with a condenser, stirrer, thermometer and dropping funnel with nitrogen inlet was charged with 100 ml THF in which pentamethylbenzyl chloride (19.8 g, 0.10 mol) was dissolved. The solution was cooled to -20° C. and sodium cyclopentadienyl (60 ml, 2.0 M in THF) was added; the solution was stirred for 48 hours at 22° C. GC analysis showed 90% conversion to pentamethylcyclopentadienyl. A precipitate was filtered off and the solvent was evaporated. The remaining residue was recrystallized from hot dichloromethane/petroleum ether. After recrystallization, pentamethylcyclopentadiene (16 g) was obtained. The product was characterized by GC, GC-MS, 13C and 1H NMR.
Workup
- customA 250 ml roundbottom flask equipped with a condenser, stirrer
- dissolutionwas dissolved
- filtrationA precipitate was filtered off
- customthe solvent was evaporated
- customThe remaining residue was recrystallized from hot dichloromethane/petroleum ether
- customAfter recrystallization
Sources & evidence
- ORD record
- ord-dc352001f89f41128bf5d452adeac725
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05986029
Reaction notes
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