[3-(hydroxymethyl)-5-methoxyphenyl]methanol

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 5.00 g (22.32 mmoles) of methyl,methyl 5-methoxyisophthalate in 100 ml dry THF is added dropwise, maintaining a gentle reflux, 67 ml (66.96 mmoles) of a 1M solution of lithium aluminum hydride in Et2O. After addition the reaction mixture is stirred for 1 hour and is then quenched with saturated NH4Cl. The reaction mixture is then extracted with Et2O (3 times). The Et2O layers are combined, washed with brine, dried with MgSO4, filtered and concentrated down in vacuo to yield 1,3-di-(hydroxymethyl)-5-methoxybenzene which is used directly in the next step. After addition the reaction mixture is then quenched with saturated NH4Cl The reaction mixture is then extracted with Et2O (3 times) washed with brine dried with MgSO4 filtered concentrated down in vacuo

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

Procedure: To a solution of 1g of 5-methoxy-1,3-benzenedimethanol in 10 ml of DMF there was added 238 mg of sodium hydride (60% oily suspension) at 0° C. After stirring at room temperature for 30 minutes, 1.04 g of 1-fluoro-2-iodoethane was added and the mixture was stirred at room temperature for 22 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (145 mg) as a colorless oil. the mixture was stirred at room temperature for 22 hours The organic layer was washed with water and saturated brine dried over anhydrous sodium sulfate The desiccating agent was filtered off the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate-heptane)

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

Procedure: To a solution of 1 g of 5-methoxy-1,3-benzenedimethanol in 10 ml of DMF there was added 238 mg of sodium hydride (60% oily suspension) at 0° C. After stirring at room temperature for 30 minutes, 1.04 g of 1-fluoro-2-iodoethane was added and the mixture was stirred at room temperature for 22 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (145 mg) as a colorless oil. the mixture was stirred at room temperature for 22 hours The organic layer was washed with water and saturated brine dried over anhydrous sodium sulfate The desiccating agent was filtered off the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate-heptane)

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

Procedure: Carbon tetrabromide (3.47 g) was added to a stirred solution of 1,3-dihydroxymethyl-5-methoxy-benzene (800 mg) in anhydrous dichloromethane (16 mL) under argon. After cooling the resulting solution at 0° C., a solution of triphenylphosphine (2.68 g) in anhydrous dichloromethane (16 mL) was added dropwise. The reaction mixture was stirred at room temperature for 20 h and then concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioPrep 90 g column, Si60 15-40 μm, eluted with methanol/dichloromethane, 4:96) to give 1-bromomethyl-3-hydroxymethyl-5-methoxy-benzene (420 mg): concentrated in vacuo to a residue The residue was purified by silica gel chromatography (Merck SuperVarioPrep 90 g column, Si60 15-40 μm, eluted with methanol/dichloromethane, 4:96)

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

Procedure: To a solution of 1 g of 5-methoxy-1,3-benzenedimethanol in 10 ml of DMF there was added 238 mg of sodium hydride (60% oily suspension) at 0° C. After stirring at room temperature for 30 minutes, 1.04 g of 1-fluoro-2-iodoethane was added and the mixture was stirred at room temperature for 22 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (145 mg) as a colorless oil. the mixture was stirred at room temperature for 22 hours The organic layer was washed with water and saturated brine dried over anhydrous sodium sulfate The desiccating agent was filtered off the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate-heptane)