3005 Synthesis of 7,7-dichlorobicyclo[4.1.0]heptane (7,7-dichlornorcarane) from cyclohexene
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1 00 Synthesis of,-dichlorobicyclo[..0]heptane (,-dichlornorcarane) from cyclohexene + CHCl NaOH tri-n-propylamine CCl + HCl C H 0 (8.) (9.) NaOH C 9 H N C H 0 Cl (0.0) (.) (.) (.) Classification Reaction types and substance classes addition to alkenes, elimination, cycloaddition alkene, carben, chloroalkane Work methods Stirring with magnetic stir bar, adding dropwise with addition funnel, distilling under reduced pressure, evaporating with rotary evaporator, shaking out, extracting, filtering, use of ice cooling bath, heating withn oil bath Instruction (batch scale 00 mmol) Equipment 00 ml three neck round bottom flask, reflux condenser, addition funnel with pressure balance, heatable magnetic stirrer, magnetic stir bar, thermometer for inside of the flask, separating funnel, destillation apparatus, rotary evaporator, oil bath, ice bath, vacuum pump Substances cyclohexene (bp 8 C) chloroform (bp C) sodium hydroxide tri-n-propylamine (bp C) water ethanol (bp 8 C) n-pentane (bp C) sodium sulfate for drying sodium chloride 8. g (0. ml, 00 mmol) 8.0 g (. ml, 00 mmol).0 g (00 mmol) 0. g (0.9 ml,.0 mmol) ml ml 0 ml about g about 8 g Reaction Into a 00 ml three neck round bottom flask equipped with a reflux condenser addition funnel, thermometer for measuring the inside temperature and magnetic stir bar, 8. g
2 (0. ml, 00 mmol) cyclohexene 0. g (0.9 ml,.0 mmol) tri-n-propylamine, 8.0 g (. ml, 00 mmol) chloroform and ml ethanol is added. The mixture is cooled to 0 C with an ice bath, then under stirring and further cooling in the ice bath a solution of.0 g (00 mmol) sodium hydroxide in ml water is added through an addition funnel. The mixture should be stirred vigourously during the next 0 minutes at 0 C. After this time the mixture is further stirred during hour at room temperature and hours at 0 C. Work up Chloroform is evaporated with a rotary evaporator, then the residue is transferred with about 0 ml water and 0 ml n-pentane into a separating funnel. The organic phase is separated, the aqueous phase is further extracted three times with 0 ml pentane. If an emulsion is formed the aqueous phase is saturated with NaCl. The combined organic phases are dried over sodium sulfate. The solution is filtered from sodium sulfate and the solvent is evaporated with a rotary evaporator, yielding a nearly colourless liquid as crude product. The crude yield is. g. The crude product is distilled under reduced pressure. Yield:. g (8. mmol, 8%), colourless liquid; bp C ( hpa) Waste management Waste disposal Waste evaporated chloroform (may contain some cyclohexene) evaporated n-pentane (may contain some chloroform aqueous phase, after extraction destillation residue sodium sulfate Disposal solvent water mixtures, containing halogen solid waste, free from mercury Time hours Break Before work up Degree of difficulty Easy Instruction (batch scale 0 mmol) Equipment 00 ml three neck round bottom flask, reflux condenser, addition funnel with pressure balance, heatable magnetic stirrer, magnetic stir bar, thermometer for inside of the flask, separating funnel, destillation apparatus, rotary evaporator, oil bath, ice bath, vacuum pump
3 Substances cyclohexene (bp 8 C) chloroform (bp C) sodium hydroxide tri-n-propylamine (bp C) water ethanol (bp 8 C) n-pentane (bp C) sodium sulfate for drying sodium chloride 0.8 g (.0 ml, 0.0 mmol). g (.0 ml, mmol).0 g (0.0 mmol) 0.0 g (0.0 ml, 0.0 mmol). ml 0. ml ml about g about g Reaction Into a 0 ml three neck round bottom flask equipped with a reflux condenser addition funnel, thermometer for measuring the inside temperature and magnetic stirring bar, 0.8 g (.0 ml, 00 mmol) cyclohexene 0.0 g (0.09 ml, 0. mmol) tri-n-propylamine,.8 g (0. ml, mmol) chloroform and 0. ml ethanol is added. The mixture is cooled to 0 C with an ice bath, then under stirring and further cooling of the ice bath a solution of. g (0.0 mmol) sodium hydroxide in. ml water is added by a addition funnel. The mixture should be stirred vigourously during the next 0 minutes at 0 C. After this time the mixture is further stirred during hour at room temperature and hours at 0 C. Work up Chloroform is evaporated with a rotary evaporator, then the residue is transferred with about ml water and ml n-pentane into a separating funnel. The organic phase is separated, the aqueous phase is further extracted three times with 0 ml pentane. If an emulsion is formed the aqueous phase is saturated with NaCl. The combined organic phases are dried over sodium sulfate. The solution is filtered from sodium sulfate and the solvent is evaporated with a rotary evaporator, yielding a nearly colourless liquid as crude product. The crude yield is. g. The crude product is distilled under reduced pressure. Yield. g (8. mmol, 8%), colourless liquid; bp C ( hpa) Waste management Waste disposal Waste evaporated chloroform (may contain some cyclohexene) evaporated n-pentane (may contain some chloroform aqueous phase, after extraction destillation residue sodium sulfate Disposal solvent water mixtures, containing halogen solid waste, free from mercury
4 Time hours Break Before work up Degree of difficulty Easy Instruction (batch scale mol) Equipment 00 ml three neck round bottom flask, reflux condenser, addition funnel with pressure balance, heatable magnetic stirrer, magnetic stir bar, thermometer for inside of the flask, separating funnel, destillation apparatus, rotary evaporator, oil bath, ice bath, vacuum pump Substances cyclohexene (bp 8 C) chloroform (bp C) sodium hydroxide tri-n-propylamine (bp C) water ethanol (bp 8 C) n-pentane (bp C) sodium sulfate for drying sodium chloride 8. g (0 ml,.00 mol) 80 g ( ml,.00mol) 0 g (.00 mol). g (.9 ml, 0 mmol) 0 ml 0 ml 00 ml about g about g Reaction Into a 000 ml three neck round bottom flask equipped with a reflux condenser addition funnel, thermometer for measuring the inside temperature and magnetic stir bar, 8. g (0. ml, mol) cyclohexene. g (.9 ml, 0 mmol) tri-n-propylamine, 80 g ( ml, 00 mmol) chloroform and 0 ml ethanol is added. The mixture is cooled to 0 C with an ice bath, then under stirring and further cooling of the ice bath a solution of 0 g (mol) sodium hydroxide dissolved in 0 ml water is added by a addition funnel. The mixture should be stirred vigourously during the next 0 minutes at 0 C. After this time the mixture is further stirred during hour at room temperature and hours at 0 C. Work up Chloroform is evaporated with a rotary evaporator, then the residue is transferred with about 00 ml water and 0 ml n-pentane into a separating funnel. The organic phase is separated, the aqueous phase is further extracted three times with 0 ml pentane. If an emulsion is formed the aqueous phase is saturated with sodium chloride. The combined organic phases are dried over sodium sulfate. The solution is filtered from sodium sulfate and the solvent is
5 evaporated with a rotary evaporator, yielding a nearly colourless liquid as crude product. The crude yield is.0 g.the crude product is distilled under reduced pressure. Yield: 9 g (0.8 mol, 8%), colourless liquid; bp C ( hpa) Waste management Waste disposal Waste evaporated chloroform (may contain some cyclohexene) evaporated n-pentane (may contain some chloroform aqueous phase, after extraction destillation residue sodium sulfate Disposal solvent water mixtures, containing halogen solid waste, free from mercury Time hours Break Before work up Degree of difficulty Easy Analytics GC Sample preparation: One drop of the compound is dissolved in ml tert-butyl methyl ether, µl is injected. GC conditions: column: Macherey und Nagel, SE-, -MN-00-9, m, ID 0. mm, DF 0. µm inlet: Gerstel KAS, injector 0 C; split injection: :0, injected volume µl carrier gas: nitrogen, pre-column pressure kpa, flow rate.0 ml/min oven: 80 C ( min), 0 C/min (0 C) (0 min) detector: FID, C Percent concentration was calculated from peak areas.
6 GC of the crude product Retention time (min) Substance Peak area % 8.,-dichloronorcarane 98. not identified GC of the pure product Retention time (min) Substance Peak area % 8.,-dichloronorcarane > 99
7 H NMR spectrum of the crude product (00 MHz, CDCl ) H NMR spectrum of the pure product (00 MHz, CDCl ) δ (ppm) Multiplicity Number of H Assignment. -. m -H, -H. -. m -H, -H m -H, -H. solvent CCl
8 C NMR spectrum of the crude product ( MHz, CDCl ) C NMR spectrum of the purified product ( MHz, CDCl ) δ (ppm) Assignment 8.9 C-, C- 0. C-, C-.8 C-, C-. C-.-. solvent CCl 8
9 IR spectrum of the crude product (film) IR spectrum of pure product (film) (cm - ) Assignment 9, 89 C-H-valence, alkane 9 C-Cl-valence 9
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