(2,6-dimethoxyphenyl)methanol

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

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

Procedure: After a mixture of 5.7 grams (0.034 mole) of 2,6-dimethoxyphenylmethanol in 40 mL of concentrated hydrobromic acid was stirred at ambient temperature for about one hour, the reaction mixture was taken up in diethyl ether. Solid sodium chloride was added to the mixture to obtain a phase separation. The organic layer was separated and concentrated under reduced pressure, yielding about 4.7 grams of 2,6-dimethoxyphenylmethyl bromide. This compound was used immediately in the next reaction. to obtain a phase separation The organic layer was separated concentrated under reduced pressure

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

Procedure: A solution of 2,6-Dimethoxylbenzyl alcohol (3.33 g, 19.8 mmol) and diisopropyl azodicarboxylate (DIAD, 4.36 g, 21.6 mmol) in THF (30 ml) was added drop wise to a solution of Ethyl 2-(3-hydroxyphenyl)acetate (4 g, 22.2 mmol) and triphenylphosphine (5.66 g, 21.6 mmol) in THF (80 ml). The reaction mixture was stirred at room temperature for 8 hours, diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound. washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1)

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

Procedure: A solution of 2,6-Dimethoxylbenzyl alcohol (3.33 g, 19.8 mmol) and diisopropyl azodicarboxylate (DIAD, 4.36 g, 21.6 mmol) in THF (30 ml) was added drop wise to a solution of Ethyl 2-(3-hydroxyphenyl)acetate (4 g, 22.2 mmol) and triphenylphosphine (5.66 g, 21.6 mmol) in THF (80 ml). The reaction mixture was stirred at room temperature for 8 hours, diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound. washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1)

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

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

Procedure: A solution of 2,6-Dimethoxylbenzyl alcohol (3.33 g, 19.8 mmol) and diisopropyl azodicarboxylate (DIAD, 4.36 g, 21.6 mmol) in THF (30 ml) was added drop wise to a solution of Ethyl 2-(3-hydroxyphenyl)acetate (4 g, 22.2 mmol) and triphenylphosphine (5.66 g, 21.6 mmol) in THF (80 ml). The reaction mixture was stirred at room temperature for 8 hours, diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound. washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1)

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

Procedure: After a mixture of 5.7 grams (0.034 mole) of 2,6-dimethoxyphenylmethanol in 40 mL of concentrated hydrobromic acid was stirred at ambient temperature for about one hour, the reaction mixture was taken up in diethyl ether. Solid sodium chloride was added to the mixture to obtain a phase separation. The organic layer was separated and concentrated under reduced pressure, yielding about 4.7 grams of 2,6-dimethoxyphenylmethyl bromide. This compound was used immediately in the next reaction. to obtain a phase separation The organic layer was separated concentrated under reduced pressure

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

Procedure: 1.86 g (11.1 mmol) of 2,6-dimethoxybenzyl alcohol was dissolved in 15 ml of benzene, and the resultant solution was cooled to 5° C. The solution was then added with 1.55 g (13.0mmol) of thionyl chloride at the same temperature. The mixture was subjected to temperature elevation up to a room temperature, then stirred for 70 min. to complete a reaction. The reacted solution was condensed under reduced pressure to thereby obtain a crude product of 2,6-dimethoxybenzyl chloride. was subjected to temperature elevation up to a room temperature a reaction condensed under reduced pressure

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

Procedure: 0.49 g (2.93 mmol) of 2,6-dimethoxybenzyl alcohol was dissolved in 6 ml of benzene, and the resultant solution was added with 0.41 g (3.32 mmol) of thionyl chloride at a room temperature. The thus obtained solution was then stirred for 1.5 hours at a room temperature to complete a reaction. The reacted solution was then condensed under reduced pressure to obtain a crude product of 2,6-dimethoxybenzyl chloride. a reaction condensed under reduced pressure

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

Procedure: 0.43 g (2.56 mmol) of 2,6-dimethoxybenzyl alcohol was dissolved in 5 ml of benzene, and the resultant solution was added with 0.40 g (3.36 mmol) of thionyl chloride at a room temperature. The mixture was then stirred for an hour at a room temperature to facilitate the provided compounds to react. The reacted solution was then condensed under reduced pressure to obtain a crude product of 2,6-dimethoxybenzyl chloride. to react condensed under reduced pressure

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

Procedure: After a mixture of 5.7 grams (0.034 mole) of 2,6-dimethoxyphenylmethanol in 40 mL of concentrated hydrobromic acid was stirred at ambient temperature for about one hour, the reaction mixture was taken up in diethyl ether. Solid sodium chloride was added to the mixture to obtain a phase separation. The organic layer was separated and concentrated under reduced pressure, yielding about 4.7 grams of 2,6-dimethoxyphenylmethyl bromide. This compound was used immediately in the next reaction. to obtain a phase separation The organic layer was separated concentrated under reduced pressure

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

Procedure: A solution of 2,6-Dimethoxylbenzyl alcohol (3.33 g, 19.8 mmol) and diisopropyl azodicarboxylate (DIAD, 4.36 g, 21.6 mmol) in THF (30 ml) was added drop wise to a solution of Ethyl 2-(3-hydroxyphenyl)acetate (4 g, 22.2 mmol) and triphenylphosphine (5.66 g, 21.6 mmol) in THF (80 ml). The reaction mixture was stirred at room temperature for 8 hours, diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound. washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1)