3-methyl-2,3,4,5,6,7-hexahydroinden-1-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl lithium (1.5M, 96 ml) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 ml of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture after this time period was hydrolyzed and the reaction mixture extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution, 0.5 ml of 6M HCl was added and the solution stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product. was refluxed for 18 hours the reaction mixture extracted with diethyl ether The ether extracts were dried over anhydrous MgSO4 filtered To the ether solution, 0.5 ml of 6M HCl was added After this time period the ether solution was washed with water dried over anhydrous MgSO4 filtered concentrated Distillation at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexene (27.3 g, 0.33 mol), crotonic acid (28.7 g, 0.33 mol) and polyphosphoric acid (300 ml) were mechanically stirred under a nitrogen atmosphere at 60° C. for 30 minutes. The slurry was poured into water and the aqueous solution extracted with diethyl ether. The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution and a saturated NaCl solution. The organic extract was then dried over anhydrous MgSO4. The solution was then filtered and the solvent removed under reduced pressure. The crude product was then purified via vacuum distillation (bp 87°-92° C. at 5 mm) to give 32.6 g (66 percent) of purified material. the aqueous solution extracted with diethyl ether The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution The organic extract was then dried over anhydrous MgSO4 The solution was then filtered the solvent removed under reduced pressure The crude product was then purified via vacuum distillation (bp 87°-92° C. at 5 mm)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl lithium (96 mL, 1.5M, 0.144 mol) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 mL of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture was hydrolyzed, and extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution 0.5 mL of 6M HCl was added and the solution was stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered, and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product. was refluxed for 18 hours extracted with diethyl ether The ether extracts were dried over anhydrous MgSO4 filtered To the ether solution 0.5 mL of 6M HCl was added After this time period the ether solution was washed with water dried over anhydrous MgSO4 filtered concentrated Distillation at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl lithium (96 mL, 1.5M, 0.144 mol) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 mL of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture was hydrolyzed, and extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution 0.5 mL of 6M HCl was added and the solution was stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered, and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product. was refluxed for 18 hours extracted with diethyl ether The ether extracts were dried over anhydrous MgSO4 filtered To the ether solution 0.5 mL of 6M HCl was added After this time period the ether solution was washed with water dried over anhydrous MgSO4 filtered concentrated Distillation at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexene (27.3 g, 0.33 mol), crotonic acid (28.7 g, 0.33 mol) and polyphosphoric acid (300 mL) were mechanically stirred under a nitrogen atmosphere at 60° C. for 30 minutes. The slurry was poured into water and the aqueous solution extracted with diethyl ether. The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution and a saturated NaCl solution. The organic extract was dried over anhydrous MgSO4. The solution was filtered and the solvent removed under reduced pressure. The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm) to give 32.6 g (66 percent) of purified material. the aqueous solution extracted with diethyl ether The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution The organic extract was dried over anhydrous MgSO4 The solution was filtered the solvent removed under reduced pressure The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl lithium (96 mL, 1.5M, 0.144 mol) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 mL of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture was hydrolyzed, and extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution 0.5 mL of 6M HCl was added and the solution was stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered, and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product. was refluxed for 18 hours extracted with diethyl ether The ether extracts were dried over anhydrous MgSO4 filtered To the ether solution 0.5 mL of 6M HCl was added After this time period the ether solution was washed with water dried over anhydrous MgSO4 filtered concentrated Distillation at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexene (27.3 g, 0.33 mol), crotonic acid (28.7 g, 0.33 mol) and polyphosphoric acid (300 mL) were mechanically stirred under a nitrogen atmosphere at 60° C. for 30 minutes. The slurry was poured into water and the aqueous solution extracted with diethyl ether. The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution and a saturated NaCl solution. The organic extract was dried over anhydrous MgSO4. The solution was filtered and the solvent removed under reduced pressure. The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm) to give 32.6 g (66 percent) of purified material. the aqueous solution extracted with diethyl ether The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution The organic extract was dried over anhydrous MgSO4 The solution was filtered the solvent removed under reduced pressure The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl lithium (96 mL, 1.5M, 0.144 mol) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 mL of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture was hydrolyzed, and extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution 0.5 mL of 6M HCl was added and the solution was stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered, and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product. was refluxed for 18 hours extracted with diethyl ether The ether extracts were dried over anhydrous MgSO4 filtered To the ether solution 0.5 mL of 6M HCl was added After this time period the ether solution was washed with water dried over anhydrous MgSO4 filtered concentrated Distillation at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexene (27.3 g, 0.33 mol), crotonic acid (28.7 g, 0.33 mol) and polyphosphoric acid (300 mL) were mechanically stirred under a nitrogen atmosphere at 60° C. for 30 minutes. The slurry was poured into water and the aqueous solution extracted with diethyl ether. The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution and a saturated NaCl solution. The organic extract was dried over anhydrous MgSO4. The solution was filtered and the solvent removed under reduced pressure. The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm) to give 32.6 g (66 percent) of purified material. the aqueous solution extracted with diethyl ether The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution The organic extract was dried over anhydrous MgSO4 The solution was filtered the solvent removed under reduced pressure The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl lithium (96 mL, 1.5M, 0.144 mol) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 mL of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture was hydrolyzed, and extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution 0.5 mL of 6M HCl was added and the solution was stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered, and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product. was refluxed for 18 hours extracted with diethyl ether The ether extracts were dried over anhydrous MgSO4 filtered To the ether solution 0.5 mL of 6M HCl was added After this time period the ether solution was washed with water dried over anhydrous MgSO4 filtered concentrated Distillation at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexene (27.3 g, 0.33 mol), crotonic acid (28.7 g, 0.33 mol) and polyphosphoric acid (300 mL) were mechanically stirred under a nitrogen atmosphere at 60° C. for 30 minutes. The slurry was poured into water and the aqueous solution extracted with diethyl ether. The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution and a saturated NaCl solution. The organic extract was dried over anhydrous MgSO4. The solution was filtered and the solvent removed under reduced pressure. The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm) to give 32.6 g (66 percent) of purified material. the aqueous solution extracted with diethyl ether The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution The organic extract was dried over anhydrous MgSO4 The solution was filtered the solvent removed under reduced pressure The crude product was purified via vacuum distillation (bp 87°-92° C. at 5 mm)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl lithium (96 mL, 1.5M, 0.144 mol) was added dropwise to a solution of 4,5,6,7-tetrahydro-1-methyl-indan-3-one (17.7 g, 0.118 mol) in 50 mL of diethyl ether under an argon atmosphere whereupon the reaction mixture was refluxed for 18 hours. The mixture was hydrolyzed, and extracted with diethyl ether. The ether extracts were dried over anhydrous MgSO4 and filtered. To the ether solution 0.5 mL of 6M HCl was added and the solution was stirred for one hour. After this time period the ether solution was washed with water, dried over anhydrous MgSO4, filtered, and concentrated. Distillation at reduced pressure afforded 8.0 g (45 percent) of product. was refluxed for 18 hours extracted with diethyl ether The ether extracts were dried over anhydrous MgSO4 filtered To the ether solution 0.5 mL of 6M HCl was added After this time period the ether solution was washed with water dried over anhydrous MgSO4 filtered concentrated Distillation at reduced pressure