methyl 16-hydroxyhexadecanoate

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100.26 g (0.35 mol) of methyl 16-hydroxyhexadecanoate, 0.60 g (3.5 mol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-l flask equipped with a stirrer and a dropping funnel and 32.39 g (0.385 mol) of dihydropyan was dropped thereto under stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for additional 1 hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3 and filtered. After distilling off the solvent, crude methyl 16-(2-tetrahydropyranyloxy)hexadecanoate (III-a) was obtained. equipped with a stirrer and a dropping funnel 32.39 g (0.385 mol) of dihydropyan was dropped After the completion of the addition the mixture was stirred at room temperature for additional 1 hour the reaction filtered After distilling off the solvent

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100.26 g (0.35 mol) of methyl 16-hydroxyhexadecanoate, 0.60 g (3.5 mol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-l flask equipped with a stirrer and a dropping funnel and 32.39 g (0.385 mol) of dihydropyan was dropped thereto under stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for additional 1 hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3 and filtered. After distilling off the solvent, crude methyl 16-(2-tetrahydropyranyloxy)hexadecanoate (III-a) was obtained. equipped with a stirrer and a dropping funnel 32.39 g (0.385 mol) of dihydropyan was dropped After the completion of the addition the mixture was stirred at room temperature for additional 1 hour the reaction filtered After distilling off the solvent

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

Procedure: 65.6 gm of pyridinium chlorochromate was dissolved into 400 ml of methylene chloride. To the solution was added 55 gm of methyl 16-hydroxyhexadecanoate which had been dissolved in 40 ml of methylene chloride in advance. After stirring for 2 hours at room temperature, 400 ml of anhydrous diethyl ether was added. The supernatant was removed and the insolbles were washed three times with 100 ml of anhydrous diethyl ether. The supernatant and the washing were combined together and passed through 40 gm of a silica gel column, and the eluent was concentrated under reduced pressure. The crude crystals thus obtained were purified by flash column chromatography (chloroform:hexane=4:l) to obtain 43.6 gm of methyl 15-formylpentadecanoate. The supernatant was removed the insolbles were washed three times with 100 ml of anhydrous diethyl ether the eluent was concentrated under reduced pressure The crude crystals thus obtained were purified by flash column chromatography (chloroform:hexane=4:l)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 76.3 gm of 16-hexadecanolide and 0.29 gm of 28% sodium methoxide solution were dissolved into 250 gm of methanol, and the solution was heated at 60° C. for 60 hours while stirring. The reaction mixture was cooled to deposit crystals. The crystals were collected by filtration, washed, and dried to obtain 77.5 gm of methyl 16-hydroxyhexadecanoate (yield: 90.2%). The reaction mixture was cooled The crystals were collected by filtration washed dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100.26 g (0.35 mol) of methyl 16-hydroxyhexadecanoate, 0.60 g (3.5 mol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-1 flask equipped with a stirrer and a dropping funnel and 32.39 g (0.385 mol) of dihydropyan was dropped thereto under stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for additional 1 hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3 and filtered. After distilling off the solvent, crude methyl 16-(2-tetrahydropyranyloxy)hexadecanoate (III-a) was obtained. equipped with a stirrer and a dropping funnel 32.39 g (0.385 mol) of dihydropyan was dropped After the completion of the addition the mixture was stirred at room temperature for additional 1 hour the reaction filtered After distilling off the solvent

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100.26 g (0.35 mol) of methyl 16-hydroxyhexadecanoate, 0.60 g (3.5 mol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-1 flask equipped with a stirrer and a dropping funnel and 32.39 g (0.385 mol) of dihydropyan was dropped thereto under stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for additional 1 hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3 and filtered. After distilling off the solvent, crude methyl 16-(2-tetrahydropyranyloxy)hexadecanoate (III-a) was obtained. equipped with a stirrer and a dropping funnel 32.39 g (0.385 mol) of dihydropyan was dropped After the completion of the addition the mixture was stirred at room temperature for additional 1 hour the reaction filtered After distilling off the solvent

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

Procedure: To a cooled (0° C.) solution of 16-hydroxyhexadecanoic acid (3000 mg, 10.79 mmol) in anhydrous methanol (27 ml) acetyl chloride (3.837 ml, 53.96 mmol) was added dropwise at 0° C. within 2 min, then the mixture was stirred at room temperature for 3.5 hrs under Ar-atmosphere. Subsequently the mixture was evaporated to dryness, the residue was dissolved in dichloromethane (100 ml), washed with saturated sodium bicarbonate solution (2×50 ml) and Brine solution (1×50 ml). After drying over sodium sulfate the collected organic layer was evaporated to dryness and vacuum dried at room temperature. Yield: 92% (white solid). was added dropwise at 0° C. within 2 min Subsequently the mixture was evaporated to dryness the residue was dissolved in dichloromethane (100 ml) washed with saturated sodium bicarbonate solution (2×50 ml) and Brine solution (1×50 ml) After drying over sodium sulfate the collected organic layer was evaporated to dryness and vacuum dried at room temperature

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

Procedure: Synthesis was carried out in the same manner as described in Preparation Example 20 from 16-hydroxyhexadecanoic acid and methanol to afford the title compound. Synthesis

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100.26 g (0.35 mol) of methyl 16-hydroxyhexadecanoate, 0.60 g (3.5 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane were introduced into a 1-l flask equipped with a stirrer and a dropping funnel. 32.39 g (0.385 mol) of dihydropyran was added dropwise thereto while stirring at 0° C. After the completion of the addition, the mixture was stirred at room temperature for an hour to thereby complete the reaction. Next, the reaction mixture was neutralized by adding 0.59 g (7 mmol) of NaHCO3. After filtering and removing solvent under reduced pressure; a crude product of methyl 16-(2-tetrahydropyranyloxy)hexadecanoate was obtained. equipped with a stirrer and a dropping funnel After the completion of the addition the mixture was stirred at room temperature for an hour the reaction After filtering removing solvent under reduced pressure