octadecane-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:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.2 Grams of octadecanethiol, 14.3 g of 11-bromoundecanamide, 1.7 g of potassium iodide, 20.7 g of potassium carbonate and 100 ml of N,N-dimethylacetamide were charged in a flask equipped with a stirrer, a condenser and a calcium chloride drying tube and stirred with heating at 100° C. for 5 hours. The reaction mixture was cooled to room temperature and, then, introduced into ice water, and the precipitated crystal was filtered off under reduced pressure and washed with distilled water. The crystal was recrystallized from 2-propanol to obtain 16.4 g of the desired product. m.p. 108° C. equipped with a stirrer, a condenser and a calcium chloride drying tube The reaction mixture was cooled to room temperature the precipitated crystal was filtered off under reduced pressure washed with distilled water The crystal was recrystallized from 2-propanol

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

Procedure: As described in Example 17, but using 63 g of 1-octadecylmercaptan (0.22 mol) dissolved in 30 ml of N-methylpyrrolidone, S-octadecyl thiocarbamate was obtained in a yield of 60% of theory.

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

Procedure: 3-Bromo-2-methoxy-2-methylpropan-1-ol is reacted with the sodium salt of octadecanethiol in ethanol. The 2-methylene-3-octadecylthiopropan-1-ol (wax-like substance) is thereby obtained with the splitting off of methanol.

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

Procedure: Instead of octadecyl bromide, there can also be used octadecyl mercaptan which is then reacted with methyl 3-bromopropionate or added on to methyl acrylate with sodium methylate catalysis. In both cases, methyl 3-octadecylthiopropionate is obtained.

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

Procedure: 1-Octadecanethiol, 250 g. (0.87 mole), was dissolved in 250 ml of bis-(2-methoxyethyl) ether. Three grams (0.13 mole) of cut sodium spheres were added and the reaction mixture was transferred to a rocking autoclave and ~462 g. of ethylene oxide was bled into the autoclave over a period of 3 hours at 140°-160° C. The maximum pressure observed was 540 lbs. After all the ethylene oxide had been added, rocking was continued for an additional hour. The mixture was cooled, the bis-(2-methoxyethyl) ether was evaporated under reduced pressure, and the residue crystallized from hexane to give a white solid in 65% yield based on the octadecane thiol. rocking was continued for an additional hour The mixture was cooled the bis-(2-methoxyethyl) ether was evaporated under reduced pressure the residue crystallized from hexane to give a white solid in 65% yield

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

Procedure: 1-Octadecanethiol, 250 g. (0.87 mole), was dissolved in 250 ml of bis-(2-methoxyethyl) ether. Three grams (0.13 mole) of cut sodium spheres were added and the reaction mixture was transferred to a rocking autoclave and ~462 g. of ethylene oxide was bled into the autoclave over a period of 3 hours at 140°-160° C. The maximum pressure observed was 540 lbs. After all the ethylene oxide had been added, rocking was continued for an additional hour. The mixture was cooled, the bis-(2-methoxyethyl) ether was evaporated under reduced pressure, and the residue crystallized from hexane to give a white solid in 65% yield based on the octadecane thiol. rocking was continued for an additional hour The mixture was cooled the bis-(2-methoxyethyl) ether was evaporated under reduced pressure the residue crystallized from hexane to give a white solid in 65% yield

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a heated (40° C.) solution of 20.1 g (0.97 mole) of n-octadecanethiol in 200 ml of dried 1.2-dimethoxyethane was slowly added under argon 0.07 mole (3.4 g., 50%) of sodium hydride (rinsed with hexane to remove the mineral oil) slurried in 1,2-dimethoxyethane. The reaction mixture was then heated at reflux (85° C.) with stirring for 2 hrs. A solution of 40 g. (0.07 mole) of the nonaethylene glycol monotosylate in 200 ml. 1,2-dimethoxyethane was added dropwise and the reaction mixture allowed to reflux with stirring for 16 hours. The mixture was cooled, insoluble salts were filtered, and the solvent was evaporated to yield a near quantitative yield (0.07 mole) of the thioether. rinsed with hexane to remove the mineral oil) The reaction mixture was then heated to reflux with stirring for 16 hours The mixture was cooled insoluble salts were filtered the solvent was evaporated

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a heated (40° C.) solution of 20.1 g (0.97 mole) of n-octadecanethiol in 200 ml of dried 1.2-dimethoxyethane was slowly added under argon 0.07 mole (3.4 g., 50%) of sodium hydride (rinsed with hexane to remove the mineral oil) slurried in 1,2-dimethoxyethane. The reaction mixture was then heated at reflux (85° C.) with stirring for 2 hrs. A solution of 40 g. (0.07 mole) of the nonaethylene glycol monotosylate in 200 ml. 1,2-dimethoxyethane was added dropwise and the reaction mixture allowed to reflux with stirring for 16 hours. The mixture was cooled, insoluble salts were filtered, and the solvent was evaporated to yield a near quantitative yield (0.07 mole) of the thioether. rinsed with hexane to remove the mineral oil) The reaction mixture was then heated to reflux with stirring for 16 hours The mixture was cooled insoluble salts were filtered the solvent was evaporated

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

Procedure: The procedure of Example 10 is repeated using 8.72 g (28.5 mmol) of 1-isobutyl-2,8-dichloro-3,7,9-trioxa-1-aza-2,8-diphosphaspiro[4.5]decane, 16.33 g (57 mmol) of n-octadecyl mercaptan and 8.74 mL (63 mmol) of triethylamine in 200 mL of toluene. A white solid (7.11 g) is isolated. The product is identified by mass spectroscopy: m/z=805.