2,2,6-trimethylcyclohexan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: If the procedure of Example 8 is followed but instead of 28 g of 2,2,6-trimethyl-cyclohexanone 31 g of 2,2,3,6-tetramethyl-cyclohexanol are employed, fractional distillation gives 9.6 g of unconverted tetramethyl-cyclohexanone and 21 g (corresponding to 73% of theory, based on ketone converted) of 2,2,3,6-tetramethyl-1-(but-1'-yn-3'-en-1'-yl)-cyclohexanol of boiling point 66°-67° C/0.2 mm Hg and refractive index nD25 = 1.5018. Fragrance note: faintly floral, coniferous, fruity. fractional distillation

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

Procedure: 28 g of 2,2,6-trimethyl-cyclohexanone are added dropwise to a suspension of Na vinylacetylide (prepared from 25 g of 1,4-dichlorobut-2-ene and 15 g of Na in liquid ammonia) in 200 ml of THF, whilst cooling, and the reaction mixture is stirred overnight at room temperature. 50 ml of water are then added, the aqueous phase is extracted with ether and the resulting organic phase is dried and concentrated. Subsequent fractional distillation gives 5.5 g of unconverted trimethylcyclohexanone and 20.7 g (corresponding to 68% of theory, based on ketone converted) of 2,2,6-trimethyl-1-(but-1'-yn-3'-en-1'-yl)-cyclohexanol of boiling point 62°-63° C/0.3 mm Hg and refractive index nD25 = 1.4982. Fragrance note: fresh, tart-woody, coniferous. whilst cooling the aqueous phase is extracted with ether the resulting organic phase is dried concentrated Subsequent fractional distillation

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: In a three-necked vessel of 250 ml equipped with a thermometer, a condenser and a dropping funnel, there were placed 23.9 g (0.427M) of finely ground KOH and 50 ml of anhydrous diethyl ether. 14 G (0.1M) of 2,6,6-trimethylcyclohexanone and 13.5 g (0.138M) of hex-1-yn-3-ol were then added dropwise to the obtained suspension. The addition is slightly exothermic. After standing for 24 h, the mixture was poured onto ice and extracted with ether while the combined extracts were washed with a 10% HCl solution, with brine until neutrality and finally dried over Na2SO4 and concentrated. A fractional distillation of the obtained residue gave 12 g of 1-(1-hydroxy-2,6,6-trimethylcyclohexyl)-hex-1-yn-3-ol having b.p. 100°-125°/13.3 Pa. In a three-necked vessel of 250 ml equipped with a thermometer, a condenser and a dropping funnel, there The addition the mixture was poured onto ice extracted with ether while the combined extracts were washed with a 10% HCl solution, with brine until neutrality finally dried over Na2SO4 concentrated A fractional distillation of the obtained residue

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

Procedure: the addition of hex-1-yn-3-ol to 2,6,6-trimethylcyclohexanone to give 1-(1-hydroxy-2,6,6-trimethylcyclohexyl)-hex-1-yn-3-ol;

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

Procedure: the addition of hex-1-yn-3-ol to 2,6,6-trimethylcyclohexanone to give 1-(1-hydroxy-2,6,6-trimethylcyclohexyl)-hex-1-yn-3-ol;

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

Procedure: If the procedure of Example 8 is followed but instead of 28 g of 2,2,6-trimethyl-cyclohexanone 31 g of 2,2,3,6-tetramethyl-cyclohexanol are employed, fractional distillation gives 9.6 g of unconverted tetramethyl-cyclohexanone and 21 g (corresponding to 73% of theory, based on ketone converted) of 2,2,3,6-tetramethyl-1-(but-1'-yn-3'-en-1'-yl)-cyclohexanol of boiling point 66°-67° C/0.2 mm Hg and refractive index nD25 = 1.5018. Fragrance note: faintly floral, coniferous, fruity. fractional distillation

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

Procedure: 28 g of 2,2,6-trimethyl-cyclohexanone are added dropwise to a suspension of Na vinylacetylide (prepared from 25 g of 1,4-dichlorobut-2-ene and 15 g of Na in liquid ammonia) in 200 ml of THF, whilst cooling, and the reaction mixture is stirred overnight at room temperature. 50 ml of water are then added, the aqueous phase is extracted with ether and the resulting organic phase is dried and concentrated. Subsequent fractional distillation gives 5.5 g of unconverted trimethylcyclohexanone and 20.7 g (corresponding to 68% of theory, based on ketone converted) of 2,2,6-trimethyl-1-(but-1'-yn-3'-en-1'-yl)-cyclohexanol of boiling point 62°-63° C/0.3 mm Hg and refractive index nD25 = 1.4982. Fragrance note: fresh, tart-woody, coniferous. whilst cooling the aqueous phase is extracted with ether the resulting organic phase is dried concentrated Subsequent fractional distillation

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

Procedure: 28 g of 2,2,6-trimethyl-cyclohexanone are added dropwise to a suspension of Na vinylacetylide (prepared from 25 g of 1,4-dichlorobut-2-ene and 15 g of Na in liquid ammonia) in 200 ml of THF, whilst cooling, and the reaction mixture is stirred overnight at room temperature. 50 ml of water are then added, the aqueous phase is extracted with ether and the resulting organic phase is dried and concentrated. Subsequent fractional distillation gives 5.5 g of unconverted trimethylcyclohexanone and 20.7 g (corresponding to 68% of theory, based on ketone converted) of 2,2,6-trimethyl-1-(but-1'-yn-3'-en-1'-yl)-cyclohexanol of boiling point 62°-63° C/0.3 mm Hg and refractive index nD25 = 1.4982. Fragrance note: fresh, tart-woody, coniferous. whilst cooling the aqueous phase is extracted with ether the resulting organic phase is dried concentrated Subsequent fractional distillation

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

Procedure: In a three-necked vessel of 250 ml equipped with a thermometer, a condenser and a dropping funnel, there were placed 23.9 g (0.427M) of finely ground KOH and 50 ml of anhydrous diethyl ether. 14 G (0.1M) of 2,6,6-trimethylcyclohexanone and 13.5 g (0.138M) of hex-1-yn-3-ol were then added dropwise to the obtained suspension. The addition is slightly exothermic. After standing for 24 h, the mixture was poured onto ice and extracted with ether while the combined extracts were washed with a 10% HCl solution, with brine until neutrality and finally dried over Na2SO4 and concentrated. A fractional distillation of the obtained residue gave 12 g of 1-(1-hydroxy-2,6,6-trimethylcyclohexyl)-hex-1-yn-3-ol having b.p. 100°-125°/13.3 Pa. In a three-necked vessel of 250 ml equipped with a thermometer, a condenser and a dropping funnel, there The addition the mixture was poured onto ice extracted with ether while the combined extracts were washed with a 10% HCl solution, with brine until neutrality finally dried over Na2SO4 concentrated A fractional distillation of the obtained residue