2-methoxypropane-1,3-diol

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

Procedure: 20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4 N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product. under cooling with ice After extraction with ether the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate concentrated purified

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

Procedure: 2-Methylglycerol (10.6 g) and 10.7 g of 1-bromoheptadecane were reacted and worked up in accordance with Example 5-(i) to give 5.2 g of the above-identified alcohol compound.

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

Procedure: 2-Methylglycerol (10.6 g) and 10.7 g of 1-bromoheptadecane were reacted and worked up in accordance with Example 5-(i) to give 5.2 g of the above-identified alcohol compound.

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

Procedure: In a mixture of 30 ml of dimethyl sulfoxide (DMSO) and 30 ml of tetrahydrofuran (THF) were dissolved 10.9 g of 2-methylglycerol and 10 g of 1-bromopentadecane, and 7.7 g of powdered KOH was added at room temperature. The mixture was stirred vigorously for 30 minutes, refluxed for 3.5 hours, poured into 400 ml of water, neutralized with concentrated hydrochloric acid with ice-cooling, and extracted three times with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The oily residue (10 g) was purified by silica gel column chromatography [silica gel: 110 g; eluent: n-hexane-chloroform (2:3)] to give 4.6 g of the above-identified alcohol compound. was added at room temperature refluxed for 3.5 hours cooling extracted three times with ethyl acetate The extract was washed with water dried concentrated to dryness The oily residue (10 g) was purified by silica gel column chromatography [silica gel: 110 g; eluent: n-hexane-chloroform (2:3)]

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

Procedure: In a mixture of 20 ml of dimethyl sulfoxide and 12 ml of tetrahydrofuran were dissolved 2.2 g of 3-(3,7, 11,15-tetramethyl-2,6,10,14-hexadecatetraenyl bromide and 2.3 g of 2-O-methylglycerin, and 2.0 g of powdered potassium hydroxide was added. The mixture was stirred for 2 hours, poured into cold water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by chromatography on a silica gel column to give 1.15 g of the above-identified compound as light-yellow liquid. was added extracted with ethyl acetate The extract was washed with water dried concentrated The residue was purified by chromatography on a silica gel column

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

Procedure: In a mixture of 20 ml of dimethyl sulfoxide and 12 ml of tetrahydrofuran were dissolved 2.2 g of 3-(3,7, 11,15-tetramethyl-2,6,10,14-hexadecatetraenyl bromide and 2.3 g of 2-O-methylglycerin, and 2.0 g of powdered potassium hydroxide was added. The mixture was stirred for 2 hours, poured into cold water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by chromatography on a silica gel column to give 1.15 g of the above-identified compound as light-yellow liquid. was added extracted with ethyl acetate The extract was washed with water dried concentrated The residue was purified by chromatography on a silica gel column

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

Procedure: 20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4 N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product. under cooling with ice After extraction with ether the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate concentrated purified

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

Procedure: 20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4 N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product. under cooling with ice After extraction with ether the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate concentrated purified

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

Procedure: 2-Methylglycerol (10.6 g) and 10.7 g of 1-bromoheptadecane were reacted and worked up in accordance with Example 5-(i) to give 5.2 g of the above-identified alcohol compound.

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

Procedure: 20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product. under cooling with ice After extraction with ether the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate concentrated purified

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

Procedure: 20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product. under cooling with ice After extraction with ether the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate concentrated purified

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

Procedure: 20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product. under cooling with ice After extraction with ether the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate concentrated purified