2-butylpropane-1,3-diol

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: To 300 ml of toluene were added 20.2 g (97.0 mmol) of the 4-(4-oxocyclohexyl)cyclohexanecarbaldehyde described above, 12.8 g (96.8 mmol) of 2-n-butyl-1,3-propanediol, and 1 g of p-toluenesulfonic acid, and the mixture was refluxed by using a Dean-Stark for 2 hours. Water in an amount of 200 ml was added to the reaction solution, the product thus formed was extracted with toluene, the extract was washed with saturated aqueous bicarbonate solution and water in this turn, and then the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1), the solvent was distilled off. The residue was Silo recrystallized from ethanol to give 3.2 g (9.9 mmol) of 2-(4-(4-oxocyclohexyl)-cyclohexyl)-5-n-butyl-1,3-dioxane. Yield of this compound based on 4-(4-oxocyclohexyl)cyclohexanecarbaldehyde was 10%. the mixture was refluxed for 2 hours the product thus formed was extracted with toluene the extract was washed with saturated aqueous bicarbonate solution and water in this turn the solvent was distilled off After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1) the solvent was distilled off recrystallized from ethanol

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

Procedure: A mixture of 2-n-butylpropane-1,3-diol (6.6 g, 0.05 m) and p-(4'-n-butylbenzoyloxy)benzaldehyde (14.2 g, 0.05 m), benzene (100 ml) and a catalytic amount of 4-toluenesulfonic acid was azeotropically refluxed until no more water was collected. The solvent was evaporated and the residue was crystallized from ethanol to yield p-(5-n-butyl-1,3-dioxan-2-yl)phenyl p-n-butylbenzoate (13.4 g 67%) CN 79.2°-80.2° C., NL 160° C. was collected The solvent was evaporated the residue was crystallized from ethanol

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

Procedure: A mixture of 2.2 g of trans-4-(3,4-difluorophenyl)-cyclohexanecarbaldehyde (obtainable by converting the corresponding acid into the chloride and Rosenmund reduction), 1.32 g of 2-butylpropane-1,3-diol, 0.01 g of p-toluenesulfonic acid and 15 ml of toluene is boiled on a water separator for 3 hours, cooled, washed with water and evaporated, to give 2-[trans-4-(3,4-difluorophenyl)cyclohexyl]-5-butyl-1,3-dioxane. cooled washed with water evaporated

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

Procedure: 2-(3,5-Difluoro-4-cyanophenyl)-5-butyl-1,3-dioxane is obtained analogously to Example 1 using 5-butyl-1,3-dioxane-2-carboxylic acid chloride (obtainable by reacting ethyl glyoxylate with 2-butylpropane-1,3-diol to give ethyl 5-butyl-1,3-dioxane-2-carboxylate, saponifying the latter and reacting the resulting free acid with SOCl2).

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

Procedure: A mixture of 17.45 g of 2-butyl-1,3-propanediol, 26.4 g of diethyl (ethoxymethylidene)-malonate, 250 ml of toluene and 0.285 g of p-toluenesulfonic acid monohydrate was heated to boiling for 1 hour, with moist toluene being distilled off and replaced by the addition of fresh toluene. The reaction mixture was neutralized with triethylamine and, after cooling, washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The crude product (42.35 g) was chromatographed on 520 g of silica gel with hexane/ethyl acetate (4:1). 33.0 g of oily diethyl (5-butyl-1,3-dioxan-2-yl)-malonate were obtained. was heated distilled off replaced by the addition of fresh toluene after cooling washed with saturated sodium chloride solution dried over sodium sulphate concentrated The crude product (42.35 g) was chromatographed on 520 g of silica gel with hexane/ethyl acetate (4:1)