nonan-3-ol

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: The mesylate of 3-nonanol (11.5 g, 51.9 mmol), triiodophenol (24.5 g, 51.9 mmol) and potassium carbonate (7.18 g, 51.9 mmol) were reacted in dry DMF (200 ml) as per 2-(2,4,6-triiodophenoxy)-pentadecane except at an oil bath temperature of 87° C. for 16 hrs. The reaction was processed as for 2-(2,4,6-triiodophenoxy)-pentadecane to provide a light brown oil. Flash column chromatography (silica, hexanes) provided 3-(2,4,6-Triiodophenoxy)-nonane (20.9 g, 67%) as a clear viscous oil. to provide a light brown oil

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

Procedure: 20 g (138.6 mmol) of 3-nonanol and 15.43 g of triethylamine are dissolved in 150 ml of dichloromethane and admixed dropwise with 17.47 g (152.5 mmol) of mesyl chloride. The mixture is stirred at room temperature for 4 hours. The organic phase is extracted twice with water and dried over sodium sulphate and the solvent is removed under reduced pressure. This gives 30.7 g (95%) of a yellow liquid. The organic phase is extracted twice with water dried over sodium sulphate the solvent is removed under reduced pressure

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

Procedure: 20 g (138.6 mmol) of 3-nonanol and 15.43 g of triethylamine are dissolved in 150 ml of dichloromethane and admixed dropwise with 17.47 g (152.5 mmol) of mesyl chloride. The mixture is stirred at room temperature for 4 hours. The organic phase is extracted twice with water and dried over sodium sulphate and the solvent is removed under reduced pressure. This gives 30.7 g (95%) of a yellow liquid. The organic phase is extracted twice with water dried over sodium sulphate the solvent is removed under reduced pressure

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

Procedure: 20.5 g (144 mmol) of 3-nonanone are initially charged in 200 ml of methanol, 5.45 g (144 mmol) of sodium borohydride are added a little at a time at room temperature and the mixture is stirred overnight. The solvent is removed under reduced pressure and the mixture is then acidified and extracted with dichloromethane. The organic phase is dried over sodium sulphate. Removal of the solvent gives 20 g (96%) of a colourless oil. The solvent is removed under reduced pressure extracted with dichloromethane The organic phase is dried over sodium sulphate Removal of the solvent

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

Procedure: The mesylate of 3-nonanol (11.5 g, 51.9 mmol), triiodophenol (24.5 g, 51.9 mmol) and potassium carbonate (7.18 g, 51.9 mmol) were reacted in dry DMF (200 ml) as per 2-(2,4,6-triiodophenoxy)-pentadecane except at an oil bath temperature of 87° C. for 16 hrs. The reaction was processed as for 2-(2,4,6-triiodophenoxy)-pentadecane to provide a light brown oil. Flash column chromatography (silica, hexanes) provided 3-(2,4,6-Triiodophenoxy)nonane (20.9 g, 67%) as a clear viscous oil. to provide a light brown oil

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

Procedure: When m is 1, n is 2 and p is 2, the ring system is a 2-oxabicyclo[3.2.2]nonane, another subclass of this invention. For example, compound XVp ##STR30## in which R2, R5 and R6 are methyl can be prepared by treating a Diels-Alder adduct of acrolein and isoprene with Ph3P=C(CH3)OCH3, hydrolyzing the resulting enol ether, treating the resulting ketone derivative with methyl magnesium bromide, and subjecting the resulting alcohol to epoxidation-cyclization to yield a 2-oxabicyclo[3.2.2.]nonan-7-ol, which is treated with WCH2X in which X is a halogen atom to yield the desired ether, XVp. Alternatively, 4-methyl-3-cyclohexene-1-acetic acid, as obtained by the method of Kugatova-Shemyakina et al., Chemical Abstracts, 65:10504c (1966) is treated with methyl Grignard followed by epoxidation-cyclization of the resulting alcohol to yield a 2-oxabicyclo[3.2.2]nonan-7-ol. can be prepared to yield a 2-oxabicyclo[3.2.2

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

Procedure: When m is 1, n is 2 and p is 2, the ring system is a 2-oxabicyclo[3.2.2]nonane, another subclass of this invention. For example, compound XVp ##STR30## in which R2, R5 and R6 are methyl can be prepared by treating a Diels-Alder adduct of acrolein and isoprene with Ph3P=C(CH3)OCH3, hydrolyzing the resulting enol ether, treating the resulting ketone derivative with methyl magnesium bromide, and subjecting the resulting alcohol to epoxidation-cyclization to yield a 2-oxabicyclo[3.2.2.]nonan-7-ol, which is treated with WCH2X in which X is a halogen atom to yield the desired ether, XVp. Alternatively, 4-methyl-3-cyclohexene-1-acetic acid, as obtained by the method of Kugatova-Shemyakina et al., Chemical Abstracts, 65:10504c (1966) is treated with methyl Grignard followed by epoxidation-cyclization of the resulting alcohol to yield a 2-oxabicyclo[3.2.2]nonan-7-ol. can be prepared to yield a 2-oxabicyclo[3.2.2

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

Procedure: The mesylate of 3-nonanol (11.5 g, 51.9 mmol), triiodophenol (24.5 g, 51.9 mmol) and potassium carbonate (7.18 g, 51.9 mmol) were reacted in dry DMF (200 ml) as per 2-(2,4,6-triiodophenoxy)-pentadecane except at an oil bath temperature of 87° C. for 16 hrs. The reaction was processed as for 2-(2,4,6-triiodophenoxy)-pentadecane to provide a light brown oil. Flash column chromatography (silica, hexanes) provided 3-(2,4,6-Triiodophenoxy)-nonane (20.9 g, 67%) as a clear viscous oil. to provide a light brown oil

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

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

Procedure: The mesylate of 3-nonanol (11.5 g, 51.9 mmol), triiodophenol (24.5 g, 51.9 mmol) and potassium carbonate (7.18 g, 51.9 mmol) were reacted in dry DMF (200 ml) as per 2-(2,4,6-triiodophenoxy)-pentadecane except at an oil bath temperature of 87° C. for 16 hrs. The reaction was processed as for 2-(2,4,6-triiodophenoxy)-pentadecane to provide a light brown oil. Flash column chromatography (silica, hexanes) provided 3-(2,4,6-Triiodophenoxy)-nonane (20.9 g, 67%) as a clear viscous oil. to provide a light brown oil