hexadecane-1-thiol

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: 2-Cyclohexenone (0.14 mol, 13.4 mL) was dissolved in 10 mL of 10 percent sodium hydroxide and 50 mL of THF. An equimolar amount of hexadecyl mercaptan (0.14 mol, 42.9 mL) was added to the unsaturated ketone and the mixture refluxed to produce 3-hexadecylthiocyclohexanone (70 percent yield). This product (5.23 mmol, 1.851 g) was dissolved in methanol and reduced with sodium borohydride (5.23 mmol, 0.199 g) to give a racemic mixture of 3-hexadecylthiocyclohexanol (yield 62 percent; cis:trans ratio 4:1). The phosphorylating agent was prepared by refluxing phosphorus oxychloride (0.65 mol, 60.8 mL) and 2-bromoethanol (0.38 mol, 27.0 mL) in 25 mL of trichloroethylene to produce 2-bromoethyl dichlorophosphate (yield 53 percent). The 3-hexadecylthiocyclohexanol (0.56 mmol, 0.200 g) was dissolved in diethyl ether:THF (2:1) and refluxed with the 2-bromoethyl dichlorophosphate (222 mmol, 0.3 mL) to produce 3-hexadecylthiocyclohexyl phosphoethyl bromide (yield 54 percent). The latter (0.216 mmol, 0.150 g) was dissolved in isopropyl alcohol chloroformi:DNMF (5:3.5) and heated at 65° C. with trimethylamine (0.042 mol, 2 mL) to produce the desired product, 3-hexadecylthiocyclohexyl-phosphocholine (yield 38 percent). the mixture refluxed

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

Procedure: A solution of 15 g of hexadecylmercaptan, 3.0 g of ethyl acrylate and 2 ml of triethylamine is stirred at ambient temperature for 18 hours. The solvent is evaporated and the concentrate purified by high pressure liquid chromatography, to give 19.8 g of the desired product. The solvent is evaporated the concentrate purified by high pressure liquid chromatography

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

Procedure: A solution of 15 g of hexadecylmercaptan, 3.0 g of ethyl acrylate and 2 ml of triethylamine is stirred at ambient temperature for 18 hours. The solvent is evaporated and the concentrate purified by high pressure liquid chromatography, to give 19.8 g of the desired product. The solvent is evaporated the concentrate purified by high pressure liquid chromatography

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

Procedure: To a stirred solution of 20 g of ethyl 2-[(hexadecyloxy)methyl]-2-propenoate in 60 ml of ethyl alcohol containing 10 ml of triethylamine is added 53 ml hexadecylmercaptan. Following stirring for 18 hours, the volatile components are removed and the residue is chromatographed by HPLC on silica gel using 9:1 hexanes:ethyl acetate. Fractions containing product are combined and the solvents evaporated to give 32.9 g of the desired product as a white waxy solid. the volatile components are removed the residue is chromatographed by HPLC on silica gel using 9:1 hexanes Fractions containing product the solvents evaporated

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

Procedure: To a stirred solution of 20 g of ethyl 2-[(hexadecyloxy)methyl]-2-propenoate in 60 ml of ethyl alcohol containing 10 ml of triethylamine is added 53 ml hexadecylmercaptan. Following stirring for 18 hours, the volatile components are removed and the residue is chromatographed by HPLC on silica gel using 9:1 hexanes:ethyl acetate. Fractions containing product are combined and the solvents evaporated to give 32.9 g of the desired product as a white waxy solid. the volatile components are removed the residue is chromatographed by HPLC on silica gel using 9:1 hexanes Fractions containing product the solvents evaporated

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

Procedure: A mixture of 17.7 ml of hexadecyl mercaptan, 3.0 g of ethyl acrylate and 2 ml of triethylamine is stirred overnight, the solvent evaporated and the residue purified by HPLC, to give 19.99 g of the desired compound as a white solid. the solvent evaporated the residue purified by HPLC

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

Procedure: A mixture of 17.7 ml of hexadecyl mercaptan, 3.0 g of ethyl acrylate and 2 ml of triethylamine is stirred overnight, the solvent evaporated and the residue purified by HPLC, to give 19.99 g of the desired compound as a white solid. the solvent evaporated the residue purified by HPLC

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

Procedure: To a solution of 20 g of 2-[(hexadecyloxy)methyl]-2-propenoic acid, ethyl ester and 10 ml of triethylamine in 60 ml of ethanol is added 53 ml of hexadecyl mercaptan. This mixture is stirred overnight, then the solvents removed and the residue purified by HPLC [hexane:ethyl acetate (9:1)], to give 32.9 g of the desired compound as a white waxy solid. the solvents removed the residue purified by HPLC [hexane:ethyl acetate (9:1)]

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

Procedure: To a solution of 20 g of 2-[(hexadecyloxy)methyl]-2-propenoic acid, ethyl ester and 10 ml of triethylamine in 60 ml of ethanol is added 53 ml of hexadecyl mercaptan. This mixture is stirred overnight, then the solvents removed and the residue purified by HPLC [hexane:ethyl acetate (9:1)], to give 32.9 g of the desired compound as a white waxy solid. the solvents removed the residue purified by HPLC [hexane:ethyl acetate (9:1)]

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

Procedure: The procedure used was identical to that set forth in Example 4, except that 107 g of hexadecyl mercaptan (0.417 moles) was reacted with 29.64 g of pure pentaerythritol tetraallyl ether (0.1 moles). The crude product was recrystallized three times in 300 ml of hexane yielding 57 g of white solid having a melting point 55°-57° C. The elemental analysis found: C-73.4%, H-11.9%, S-10.0%, calculated for C88H164S4 (theoretical C-73.12%, H-12.4%, S-9.64% and O-4.81%). The crude product was recrystallized three times in 300 ml of hexane yielding 57 g of white solid