3-tetradecoxypropane-1,2-diol

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

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

Procedure: A mixture of rac-1-O-tetradecylglycerol (57.7 g, 0.2 mol), tert-butyldimethylsilyl chloride (33.2 g, 0.22 mol), imidazole (30.0 g, 0.44 mol), and DMF (300 ml) was stirred at room temperature for 1 day. The solvent was evaporated to dryness in vacuo at 70° C. and the residue was partioned between H2O and diethyl ether (500 ml each). The organic layer was dried over Na2SO4 and then evaporated to dryness. The oily residue was further evaporated by using a high vacuum at 70° C. The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield). The solvent was evaporated to dryness in vacuo at 70° C. The organic layer was dried over Na2SO4 evaporated to dryness The oily residue was further evaporated at 70° C The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield)

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

Procedure: To a mixture of Solketal (66.1 g, 0.5 mol), 1-bromotetradecane (159.4 g, 0.575 mol), and DMF (800 ml) was added 60% NaH (26.0 g, 0.65 mol) in oil dispersion in 3 portions for 1 hr. The mixture was stirred at room temperature for 1 day and methanol (20 ml) was added to destroy the excess NaH. This was then poured into 1500 ml of ice-water and the aqueous layer was extracted with hexanes (2000 ml). The combined organic layers were evaporated to dryness and the oily residue was refluxed in 10% HCl/methanol (conc. HCl, 250 ml and methanol, 675 ml) for 30 min followed by stirring at room temperature overnight. The white flaky solid was filtered and washed with methanol (122 g). The additional product was obtained from the filtrate (5.7 g); Total 127.7 g (88.5%). The crude product was recrystallized from diethyl ether; Yield 99.7 g (69.1%), mp 57°-58° C. to destroy the excess NaH This was then poured into 1500 ml of ice-water the aqueous layer was extracted with hexanes (2000 ml) The combined organic layers were evaporated to dryness the oily residue was refluxed in 10% HCl/methanol (conc. HCl, 250 ml and methanol, 675 ml) for 30 min by stirring at room temperature overnight The white flaky solid was filtered washed with methanol (122 g)

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

Procedure: A mixture of rac-1-O-tetradecylglycerol (57.7 g, 0.2 mol), tert-butyldimethylsilyl chloride (33.2 g, 0.22 mol), imidazole (30.0 g, 0.44 mol), and DMF (300 ml) was stirred at room temperature for 1 day. The solvent was evaporated to dryness in vacuo at 70° C. and the residue was partioned between H2O and diethyl ether (500 ml each). The organic layer was dried over Na2SO4 and then evaporated to dryness. The oily residue was further evaporated by using a high vacuum at 70° C. The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield). The solvent was evaporated to dryness in vacuo at 70° C. The organic layer was dried over Na2SO4 evaporated to dryness The oily residue was further evaporated at 70° C The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield)

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

Procedure: To a mixture of Solketal (66.1 g, 0.5 mol), 1-bromotetradecane (159.4 g, 0.575 mol), and DMF (800 ml) was added 60% NaH (26.0 g, 0.65 mol) in oil dispersion in 3 portions for 1 hr. The mixture was stirred at room temperature for 1 day and methanol (20 ml) was added to destroy the excess NaH. This was then poured into 1500 ml of ice-water and the aqueous layer was extracted with hexanes (2000 ml). The combined organic layers were evaporated to dryness and the oily residue was refluxed in 10% HCl/methanol (conc. HCl, 250 ml and methanol, 675 ml) for 30 min followed by stirring at room temperature overnight. The white flaky solid was filtered and washed with methanol (122 g). The additional product was obtained from the filtrate (5.7 g); Total 127.7 g (88.5%). The crude product was recrystallized from diethyl ether; Yield 99.7 g (69.1%), mp 57°-58° C. to destroy the excess NaH This was then poured into 1500 ml of ice-water the aqueous layer was extracted with hexanes (2000 ml) The combined organic layers were evaporated to dryness the oily residue was refluxed in 10% HCl/methanol (conc. HCl, 250 ml and methanol, 675 ml) for 30 min by stirring at room temperature overnight The white flaky solid was filtered washed with methanol (122 g)

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

Procedure: A mixture of rac-1-O-tetradecylglycerol (57.7 g, 0.2 mol), tert-butyldimethylsilyl chloride (33.2 g, 0.22 mol), imidazole (30.0 g, 0.44 mol), and DMF (300 ml) was stirred at room temperature for 1 day. The solvent was evaporated to dryness in vacuo at 70° C. and the residue was partioned between H2O and diethyl ether (500 ml each). The organic layer was dried over Na2SO4 and then evaporated to dryness. The oily residue was further evaporated by using a high vacuum at 70° C. The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield). The solvent was evaporated to dryness in vacuo at 70° C. The organic layer was dried over Na2SO4 evaporated to dryness The oily residue was further evaporated at 70° C The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield)

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

Procedure: A mixture of rac-1-O-tetradecylglycerol (57.7 g, 0.2 mol), tert-butyldimethylsilyl chloride (33.2 g, 0.22 mol), imidazole (30.0 g, 0.44 mol), and DMF (300 ml) was stirred at room temperature for 1 day. The solvent was evaporated to dryness in vacuo at 70° C. and the residue was partioned between H2O and diethyl ether (500 ml each). The organic layer was dried over Na2SO4 and then evaporated to dryness. The oily residue was further evaporated by using a high vacuum at 70° C. The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield). The solvent was evaporated to dryness in vacuo at 70° C. The organic layer was dried over Na2SO4 evaporated to dryness The oily residue was further evaporated at 70° C The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield)

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

Procedure: To a mixture of Solketal (66.1 g, 0.5 mol), 1-bromotetradecane (159.4 g, 0.575 mol), and DMF (800 ml) was added 60% NaH (26.0 g, 0.65 mol) in oil dispersion in 3 portions for 1 hr. The mixture was stirred at room temperature for 1 day and methanol (20 ml) was added to destroy the excess NaH. This was then poured into 1500 ml of ice-water and the aqueous layer was extracted with hexanes (2000 ml). The combined organic layers were evaporated to dryness and the oily residue was refluxed in 10% HCl/methanol (conc. HCl, 250 ml and methanol, 675 ml) for 30 min followed by stirring at room temperature overnight. The white flaky solid was filtered and washed with methanol (122 g). The additional product was obtained from the filtrate (5.7 g); Total 127.7 g (88.5%). The crude product was recrystallized from diethyl ether; Yield 99.7 g (69.1%), mp 57°-58° C. to destroy the excess NaH This was then poured into 1500 ml of ice-water the aqueous layer was extracted with hexanes (2000 ml) The combined organic layers were evaporated to dryness the oily residue was refluxed in 10% HCl/methanol (conc. HCl, 250 ml and methanol, 675 ml) for 30 min by stirring at room temperature overnight The white flaky solid was filtered washed with methanol (122 g)