2-phenylmethoxypropane-1,3-diol

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:0.00; pressure:0.00; stir:

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: To a solution of 2-benzyloxy-propane-1,3-diol (5.0 g, 27.4 mmol) in 5:1 THF-DMF (200 mL) at 0° C. was added NaH (1.5 g, 2.3 eq.) followed by methyl iodide (5.1 mL, 3.0 eq.). The resulting white slurry mixture was stirred at room temperature over weekend. The reaction mixture was quenched with sat. NH4Cl, extracted with EtOAc, dried over Na2SO4, filtered, concentrated and the product was purified by chromatography (50% EtOAc/hexanes) to give (2-methoxy-1-methoxymethyl-2-ethoxymethyl)-benzene (5.6 g, 97%). The reaction mixture was quenched with sat. NH4Cl extracted with EtOAc dried over Na2SO4 filtered concentrated the product was purified by chromatography (50% EtOAc/hexanes)

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

Procedure: To a solution of 2-benzyloxy-propane-1,3-diol (5.0 g, 27.4 mmol) in 5:1 THF-DMF (200 mL) at 0° C. was added NaH (1.5 g, 2.3 eq.) followed by methyl iodide (5.1 mL, 3.0 eq.). The resulting white slurry mixture was stirred at room temperature over weekend. The reaction mixture was quenched with sat. NH4Cl, extracted with EtOAc, dried over Na2SO4, filtered, concentrated and the product was purified by chromatography (50% EtOAc/hexanes) to give (2-methoxy-1-methoxymethyl-2-ethoxymethyl)-benzene (5.6 g, 97%). The reaction mixture was quenched with sat. NH4Cl extracted with EtOAc dried over Na2SO4 filtered concentrated the product was purified by chromatography (50% EtOAc/hexanes)

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

Procedure: To a suspension of about 26.07 g of washed about 50% sodium hydride in about 1000 ml of dimethylformamide was added about 90 g of 2-(benzyloxy)-1,3-propanediol with stirring under argon. An about 187.88 g portion of octadecyl iodide and about 150 ml of tetrahydrofuran were added and the thick mixture was stirred with a glass rod, and then with magnetic stirring for about 3 hours. Water was then added and the mixture was extracted with ether. The ether extract was washed with brine, dried and filtered through a pad of florisil. The solvent was removed and the residue chromatographed on florisil, eluting first with petroleum ether, then with about 10% ether in petroleum ether and finally eluting the product with about 30% ether in petroleum ether, giving about 73.3 g of the desired title compound as a waxy solid. the thick mixture was stirred with a glass rod with magnetic stirring for about 3 hours the mixture was extracted with ether The ether extract was washed with brine dried filtered through a pad of florisil The solvent was removed the residue chromatographed on florisil eluting first with petroleum ether with about 10% ether in petroleum ether and finally eluting the product with about 30% ether in petroleum ether

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

Procedure: To a suspension of about 14.26 g of washed about 50% sodium hydride in about 500 ml of dimethylformamide was added about 49.2 g of 2-(benzyloxy)-1,3-propanediol over about 20 minutes. The mixture was stirred for about 40 minutes, then cooled to about 0° C. and about 95.13 g of hexadecyl iodide were added. After standing about 10 minutes, the mixture was stirred at room temperature for about 3 hours, then filtered through celite and diluted with about 1000 ml of water. This mixture was extracted with petroleum ether. The ether extract was dried and the solvent removed giving an oil. This oil was chromatographed on a column of florisil, eluting first with petroleum ether and then successively with about 5% and about 10% ether in petroleum ether to elute the product, giving about 28.8 g of the desired title compound as a light yellow oil. After standing about 10 minutes the mixture was stirred at room temperature for about 3 hours filtered through celite diluted with about 1000 ml of water This mixture was extracted with petroleum ether The ether extract was dried the solvent removed giving an oil This oil was chromatographed on a column of florisil eluting first with petroleum ether successively with about 5% and about 10% ether in petroleum ether to elute the product

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

Procedure: A mixture of about 338 g of 5-(benzyloxy)-2-phenyl-m-dioxane, about 1500 ml of ethanol, about 500 ml of water and about 20 ml of sulfuric acid was refluxed for about 2 hours. The ethanol was removed, the acid neutralized with solid sodium bicarbonate, the mixture steam distilled to remove benzaldehyde and then saturated with potassium carbonate. This mixture was extracted three times with ether. The ether extracts were combined, dried and evaporated. Toluene was added and evaporated. The residue was distilled via a Kugelrohr (about 0.1 mm, 170° C.) giving an oil. This oil was dissolved in about 300 ml of toluene, cooled and diluted with two volumes of petroleum ether. Refrigeration produced about 184.69 g of the desired title compound as a solid. was refluxed for about 2 hours The ethanol was removed the mixture steam distilled to remove benzaldehyde This mixture was extracted three times with ether dried evaporated Toluene was added evaporated The residue was distilled via a Kugelrohr (about 0.1 mm, 170° C.) giving an oil cooled

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

Procedure: In a mixed solution consisting of 50 ml of DMSO and 30 ml of THF were dissolved 3.64 g (20 mmole) of 2-benzylglycerin and 9.26 g (48 mmole) of octyl bromide, and 8.96 g (160 mmole) of powdered potassium hydroxide was added to the solution, followed by vigorous stirring. Two hours later, the reaction solution was poured in cold water, and the mixture was extracted with n-hexane. The extract was washed with water, dried and concentrated, followed by purification by silica-gel chromatography (eluent: n-hexane-ethyl acetate, 20:1) to give 6.22 g (77%) of the desired compound as colorless liquid. was added to the solution the mixture was extracted with n-hexane The extract was washed with water dried concentrated followed by purification by silica-gel chromatography (eluent: n-hexane-ethyl acetate, 20:1)