octanedial

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

Procedure: When the formation of the acetal is complete, the solution is neutralized under cold conditions and diluted with water. In the course of this, 1,1,8,8-tetramethoxyoctane separates out as a water-insoluble oil; it is separated off and the remaining solution is extracted with petroleum ether. The product phases are combined, freed from petroleum ether and fractionated in vacuo. This gives 322 g of 1,1,8,8-tetramethoxyoctane boiling at 147°-149° C./30, corresponding to 91.7% of theory. it is separated off the remaining solution is extracted with petroleum ether

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

Procedure: When the formation of the acetal is complete, the solution is neutralized under cold conditions and diluted with water. In the course of this, 1,1,8,8-tetramethoxyoctane separates out as a water-insoluble oil; it is separated off and the remaining solution is extracted with petroleum ether. The product phases are combined, freed from petroleum ether and fractionated in vacuo. This gives 322 g of 1,1,8,8-tetramethoxyoctane boiling at 147°-149° C./30, corresponding to 91.7% of theory. it is separated off the remaining solution is extracted with petroleum ether

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

Procedure: 262 ml of aqueous NaIO4 was added drop wise to a vigorously stirred suspension of 105 g chromatographic grade silica gel in 500 ml dichloromethane whereby a white suspension was formed. To the suspension a solution of 6.1 g cis-1,2-cyclo-octanediol in 100 ml dichloromethane was added. The reaction mixture was stirred over night at room temperature, after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane. Finally the filtrate was dried over NaSO4, after which the solvent was removed under reduced pressure. was formed after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane Finally the filtrate was dried over NaSO4 after which the solvent was removed under reduced pressure

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

Procedure: 262 ml of aqueous NaIO4 was added drop wise to a vigorously stirred suspension of 105 g chromatographic grade silica gel in 500 ml dichloromethane whereby a white suspension was formed. To the suspension a solution of 6.1 g cis-1,2-cyclo-octanediol in 100 ml dichloromethane was added. The reaction mixture was stirred over night at room temperature, after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane. Finally the filtrate was dried over NaSO4, after which the solvent was removed under reduced pressure. was formed after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane Finally the filtrate was dried over NaSO4 after which the solvent was removed under reduced pressure

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

Procedure: To a heterogeneous mixture of octane-1,8-diol (94.64 g, 0.648 mole), TEMPO (5.08 g, 0.038 mole, available from Aldrich Chemical Company, Milwaukee, Wis.), potassium bromide (3.90 g, 0.033 mole), sodium phosphate (7.80 g, 0.065 mole), disodium phosphate (9.24 g, 0.065 mole) in methylene chloride (1.3 L) and water (500 ml) was added dropwise 12% aqueous sodium hypochlorite (1,225 g) slowly over 2 hours while maintaining the temperature below 35° C. The reaction was stirred for an additional 30 minutes and the two layers were separated. The aqueous layer was extracted with methylene chloride and combined with the organic layer. The combined organic layer was washed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride and water. The organic fraction was dried over sodium sulfate, filtered and evaporated. The material was vacuum distilled 82-84° C./0.5 mm Hg to afford octane-1,8-dial (92 g, 100% yield). C8H14O2 (142.20 g/mole). bp: 82° C./0.55 mm Hg. 1HNMR (500 MHz, CDCl3): 1.35 (m, 4H), 1.63 (m, 4H), 2.43 (m, 4H), 9.76 (t, 2H) ppm. 13CNMR (125 MHz, CDCl3): 21.8, 28.9, 43.8, 202.7 ppm. IR (νmax(cm−1)): 2940, 2860, 2740, 1725, 1460, 1420, 1400. MS (m/z): 24(M-18), 98, 95, 81, 67, 57, 54, 44, 41. while maintaining the temperature below 35° C the two layers were separated The aqueous layer was extracted with methylene chloride The combined organic layer was washed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride and water The organic fraction was dried over sodium sulfate filtered evaporated distilled 82-84° C./0.5 mm Hg

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

Procedure: When the formation of the acetal is complete, the solution is neutralized under cold conditions and diluted with water. In the course of this, 1,1,8,8-tetramethoxyoctane separates out as a water-insoluble oil; it is separated off and the remaining solution is extracted with petroleum ether. The product phases are combined, freed from petroleum ether and fractionated in vacuo. This gives 322 g of 1,1,8,8-tetramethoxyoctane boiling at 147°-149° C./30, corresponding to 91.7% of theory. it is separated off the remaining solution is extracted with petroleum ether