6,6-dimethylcyclohex-2-en-1-one

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

Procedure: 6,6-Dimethyl-cyclohex-2-en-1-one, used as starting material in the above described process, can be prepared starting from isopropyl-methyl ketone and acrolein according to a condensation reaction in the presence of an acidic dehydrating agent as indicated hereinbelow: ##STR12## can be prepared

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

Procedure: 6,6-Dimethyl-cyclohex-2-en-1-one, used as starting material in the above described process, can be prepared starting from isopropyl-methyl ketone and acrolein according to a condensation reaction in the presence of an acidic dehydrating agent as indicated hereinbelow: ##STR12## can be prepared

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

Procedure: 124 G (1M) of 6,6-dimethyl-cyclohex-2-en-1-one, 200 ml of toluene and 10 ml of trifluoro-boro-etherate are placed under nitrogen atmosphere in a three-necked reaction vessel of 1000 ml capacity equipped with a thermometer and a stirrer. The mixture was cooled to 10° and 2-methyl-penta-1,3-diene was added thereto in small portions over 4 hours. After the addition was over, the mixture was left under stirring for 1 additional hour, whereupon it was hydrolyzed with an aqueous sodium carbonate solution. The excess of toluene was removed by means of a rotary evaporator under reduced pressure and the residue was distilled to give 101.7 g of the desired product having b.p. 70°-80°/26.6 Pa. A spectroscopic analysis indicated that the product obtained consisted of about 90% of isomer cis (a) and about 10% of trans (b). equipped with a thermometer and a stirrer The mixture was cooled to 10° After the addition was left The excess of toluene was removed by means of a rotary evaporator under reduced pressure the residue was distilled

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

Procedure: adding 2-methyl-penta-1,3-diene to 6,6-dimethyl-cyclohex-2-en-1-one under the conditions of a Diels-Alder type reaction to give 3,4,4a,5,8,8a-hexahydro-2,2,6,8-tetramethyl-1(2H)-naphthalenone, and under the conditions of a Diels-Alder type reaction

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

Procedure: adding 2-methyl-penta-1,3-diene to 6,6-dimethyl-cyclohex-2-en-1-one under the conditions of a Diels-Alder type reaction to give 3,4,4a,5,8,8a-hexahydro-2,2,6,8-tetramethyl-1(2H)-naphthalenone, and under the conditions of a Diels-Alder type reaction

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

Procedure: 4-Cyano-2-methylphenylboronic acid (0.81 g, 5 mmol), 6,6-dimethylcyclohex-2-enone (Canadian Journal of Chemistry, 1981, 59, 2096-2115) (0.55 g, 5 mmol), SbCl3 (0.11 g, 0.5 mmol), sodium acetate (0.82 g, 10 mmol), and palladium acetate (0.11 g, 0.5 mmol) are added to acetic acid (30 mL) under an atmosphere of argon. The reaction mixture is stirred at room temperature for three days. The mixture is filtered and the filtrate is poured into water (150 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with saturated sodium bicarbonate solution (3×100 mL), brine (3×50 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with pet ether: EtOAc=10:1 to give the title compound as a light yellow solid (0.6 g, 50%). GC/MS 241 (M+1). The mixture is filtered the filtrate is poured into water (150 mL) The organic phase is separated the aqueous phase is extracted with ethyl acetate (3×100 mL) The combined organic layers are washed with saturated sodium bicarbonate solution (3×100 mL), brine (3×50 mL) dried over anhydrous sodium sulfate concentrated in vacuo The residue is purified by silica gel column chromatography eluting with pet ether

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

Procedure: 6,6-Dimethyl-cyclohex-2-en-1-one, used as starting material in the above described process, can be prepared starting from isopropyl-methyl ketone and acrolein according to a condensation reaction in the presence of an acidic dehydrating agent as indicated hereinbelow: ##STR12## can be prepared

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

Procedure: 124 G (1M) of 6,6-dimethyl-cyclohex-2-en-1-one, 200 ml of toluene and 10 ml of trifluoro-boro-etherate are placed under nitrogen atmosphere in a three-necked reaction vessel of 1000 ml capacity equipped with a thermometer and a stirrer. The mixture was cooled to 10° and 2-methyl-penta-1,3-diene was added thereto in small portions over 4 hours. After the addition was over, the mixture was left under stirring for 1 additional hour, whereupon it was hydrolyzed with an aqueous sodium carbonate solution. The excess of toluene was removed by means of a rotary evaporator under reduced pressure and the residue was distilled to give 101.7 g of the desired product having b.p. 70°-80°/26.6 Pa. A spectroscopic analysis indicated that the product obtained consisted of about 90% of isomer cis (a) and about 10% of trans (b). equipped with a thermometer and a stirrer The mixture was cooled to 10° After the addition was left The excess of toluene was removed by means of a rotary evaporator under reduced pressure the residue was distilled

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

Procedure: adding 2-methyl-penta-1,3-diene to 6,6-dimethyl-cyclohex-2-en-1-one under the conditions of a Diels-Alder type reaction to give 3,4,4a,5,8,8a-hexahydro-2,2,6,8-tetramethyl-1(2H)-naphthalenone, and under the conditions of a Diels-Alder type reaction