octadecanoyl octadecanoate

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

Procedure: When the reaction was completed, spent MAPP gas was removed from the product mixture in flash chamber 14. Gases were vented overhead and a liquid seal (not shown) was maintained at the bottom drain 15 to prevent leakage of spent gases into the atmosphere. A sight glass was provided in the barricade to permit remote manual control of the liquid level in chamber 14. Liquid exiting from the flash chamber was at a temperature of about 280° F and contained no apparent dissolved gas. Since isopropenyl stearate reacts slowly with stearic acid to form stearic anhydride the reaction was quenched by rapidly solidifying the product on double drum flaker 16. Drum clearance was 0.044 inches and the drums were cooled by circulating water at a temperature of about 50° F at a rate of about 2.9 gallons per minute. The product, an amorphous solid, was scraped from the drums with doctor blades. was removed from the product mixture in flash chamber 14 a liquid seal (not was maintained at the bottom drain 15 A sight glass was provided in the barricade was at a temperature of about 280° F no apparent dissolved gas

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Matairesinol (500 mg, 1.4 mmol) was dissolved in 25 ml pyridine. To the solution stearic acid anhydride (3.1 g, 5.6 mmol) was added in small portions. The temperature was raised to 65° C. and the mixture was stirred for 24 h. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. Unreacted stearic anhydride and stearic acid precipitated from the dichloromethane solution and were filtered off. The solvent was then removed and the residue was washed with n-hexane to afford matairesinol stearate as a white solid. Yield 514 mg, 41%. Purity approximately 90%, consisting of some free stearic acid and acid anhydride (NMR). The solvent was removed under reduced pressure the residue dissolved in dichloromethane precipitated from the dichloromethane solution were filtered off The solvent was then removed the residue was washed with n-hexane

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

Procedure: When the reaction was completed, spent MAPP gas was removed from the product mixture in flash chamber 14. Gases were vented overhead and a liquid seal (not shown) was maintained at the bottom drain 15 to prevent leakage of spent gases into the atmosphere. A sight glass was provided in the barricade to permit remote manual control of the liquid level in chamber 14. Liquid exiting from the flash chamber was at a temperature of about 280° F and contained no apparent dissolved gas. Since isopropenyl stearate reacts slowly with stearic acid to form stearic anhydride the reaction was quenched by rapidly solidifying the product on double drum flaker 16. Drum clearance was 0.044 inches and the drums were cooled by circulating water at a temperature of about 50° F at a rate of about 2.9 gallons per minute. The product, an amorphous solid, was scraped from the drums with doctor blades. was removed from the product mixture in flash chamber 14 a liquid seal (not was maintained at the bottom drain 15 A sight glass was provided in the barricade was at a temperature of about 280° F no apparent dissolved gas

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

Procedure: When the reaction was completed, spent MAPP gas was removed from the product mixture in flash chamber 14. Gases were vented overhead and a liquid seal (not shown) was maintained at the bottom drain 15 to prevent leakage of spent gases into the atmosphere. A sight glass was provided in the barricade to permit remote manual control of the liquid level in chamber 14. Liquid exiting from the flash chamber was at a temperature of about 280° F and contained no apparent dissolved gas. Since isopropenyl stearate reacts slowly with stearic acid to form stearic anhydride the reaction was quenched by rapidly solidifying the product on double drum flaker 16. Drum clearance was 0.044 inches and the drums were cooled by circulating water at a temperature of about 50° F at a rate of about 2.9 gallons per minute. The product, an amorphous solid, was scraped from the drums with doctor blades. was removed from the product mixture in flash chamber 14 a liquid seal (not was maintained at the bottom drain 15 A sight glass was provided in the barricade was at a temperature of about 280° F no apparent dissolved gas

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

Procedure: A solution of stearic anhydride (1.14 g, 2.06 mmol) in dichloromethane (30 mL) was cannulated into a stirred solution of ethylene glycol (1.10 mL, 19.7 mmol), DMAP (22 mg, 0.18 mmol) and triethylamine (0.300 mL, 2.16 mmol) in dichloromethane (20 mL). After stirring for 90 min. the reaction was quenched with the addition of H2O (100 mL). After separation of the phases the aqueous fraction was re-extracted with dichloromethane (2×50 mL) and the combined organic extract was washed with brine (70 mL). After drying (MgSO4) and filtration the solvent was removed at reduced pressure to give the crude product that was purified by chromatography on silica gel. Gradient elution with ethyl acetate/petroleum ether (10:90→30:70) afforded the title compound 48 (265 mg, 0.807 mmol, 39%) as an oil; 1H NMR (300 MHz, CDCl3) δ 4.25-4.20 (m, 2H), 3.83-3.78 (m, 2H), 2.38 (t, 2H, J 7.5 Hz), 2.00-1.97 (m, 1H), 1.62-1.55 (m, 2H), 1.35-1.20 (m, 28H), 0.87-0.81 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 174.6, 66.3, 61.7, 34.6, 32.3, 30.1, 29.8, 29.7, 29.6, 29.5, 25.3, 23.1, 14.5; HRMS-ESI (+ve) (Found: m/z 346.3323 (MNH4+). C20H44NO3 requires m/z 346.3316). was quenched with the addition of H2O (100 mL) After separation of the phases the aqueous fraction was re-extracted with dichloromethane (2×50 mL) the combined organic extract was washed with brine (70 mL) After drying (MgSO4) and filtration the solvent was removed at reduced pressure to give the crude product that was purified by chromatography on silica gel Gradient elution with ethyl acetate/petroleum ether (10:90→30:70)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Matairesinol (500 mg, 1.4 mmol) was dissolved in 25 ml pyridine. To the solution stearic acid anhydride (3.1 g, 5.6 mmol) was added in small portions. The temperature was raised to 65° C. and the mixture was stirred for 24 h. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. Unreacted stearic anhydride and stearic acid precipitated from the dichloromethane solution and were filtered off. The solvent was then removed and the residue was washed with n-hexane to afford matairesinol stearate as a white solid. Yield 514 mg, 41%. Purity approximately 90%, consisting of some free stearic acid and acid anhydride (NMR). The solvent was removed under reduced pressure the residue dissolved in dichloromethane precipitated from the dichloromethane solution were filtered off The solvent was then removed the residue was washed with n-hexane

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

Procedure: When the reaction was completed, spent MAPP gas was removed from the product mixture in flash chamber 14. Gases were vented overhead and a liquid seal (not shown) was maintained at the bottom drain 15 to prevent leakage of spent gases into the atmosphere. A sight glass was provided in the barricade to permit remote manual control of the liquid level in chamber 14. Liquid exiting from the flash chamber was at a temperature of about 280° F and contained no apparent dissolved gas. Since isopropenyl stearate reacts slowly with stearic acid to form stearic anhydride the reaction was quenched by rapidly solidifying the product on double drum flaker 16. Drum clearance was 0.044 inches and the drums were cooled by circulating water at a temperature of about 50° F at a rate of about 2.9 gallons per minute. The product, an amorphous solid, was scraped from the drums with doctor blades. was removed from the product mixture in flash chamber 14 a liquid seal (not was maintained at the bottom drain 15 A sight glass was provided in the barricade was at a temperature of about 280° F no apparent dissolved gas