4-(dimethoxymethyl)phenol

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 500 ml. 4-neck flask fitted with a mechanical stirrer, thermometer, condenser and a vented nitrogen bubbler were placed 84 g. 4-dimethoxymethyl phenol (0.5 mole), 71 g. glycidyl methacrylate (GMA) (0.5 mole), and 1.5 g. benzyl tributyl ammonium chloride (0.005 mole). The apparatus was flushed with air for 5 minutes and the solution was then heated to 80° C. for 5 hours. The progress of the reaction was followed from disappearance of the GMA. Gas chromatographic analysis of the reaction mixture indicated 95% reaction. The solution was cooled and dissolved in 250 ml. methylene chloride and washed three times with lN sodium hydroxide (100 ml.) and then with water until the washings were neutral. The organic layer was dried over magnesium sulfate and the solvent was removed at reduced pressure using a Rotovap. The oily residue was dried under high vacuum for 30 minutes. The yield was 133 g. (86%) product. H-1 NMR showed signals typical of GMA except the signal for the protons that were attached to the epoxide carbon at 2.8 and 3.3 ppm showed up as doublets and a quintet respectively. The spectrum also showed signals for the 4-dimethoxymethylphenyl group at ppms 7.8-6.9 and 3.4. 4-neck flask fitted with a mechanical stirrer thermometer, condenser and a vented nitrogen bubbler were placed The apparatus was flushed with air for 5 minutes 95% reaction The solution was cooled dissolved in 250 ml methylene chloride and washed three times with lN sodium hydroxide (100 ml.) The organic layer was dried over magnesium sulfate the solvent was removed at reduced pressure The oily residue was dried under high vacuum for 30 minutes

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

Procedure: A mixture of 4.88 g (40 mmol) of 4-hydroxybenzaldehyde, 6.6 g (206 mmol) of methanol and 5.1 g (48 mmol) of trimethylorthoformate and 28 mg of p-toluene sulfonic acid was stirred at room temperature for 12 h. An excess of NaHCO3 was then added and the mixture stirred for a further 60 h. The mixture was then filtered, the solvent removed in-vacuo and the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes) to give the title compound as a viscous oil. the mixture stirred for a further 60 h The mixture was then filtered the solvent removed in-vacuo the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes)

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

Procedure: A mixture of 4.88 g (40 mmol) of 4-hydroxybenzaldehyde, 6.6 g (206 mmol) of methanol and 5.1 g (48 mmol) of trimethylorthoformate and 28 mg of p-toluene sulfonic acid was stirred at room temperature for 12 h. An excess of NaHCO3 was then added and the mixture stirred for a further 60 h. The mixture was then filtered, the solvent removed in-vacuo and the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes) to give the title compound as a viscous oil. the mixture stirred for a further 60 h The mixture was then filtered the solvent removed in-vacuo the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes)

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 500 ml. 4-neck flask fitted with a mechanical stirrer, thermometer, condenser and a vented nitrogen bubbler were placed 84 g. 4-dimethoxymethyl phenol (0.5 mole), 71 g. glycidyl methacrylate (GMA) (0.5 mole), and 1.5 g. benzyl tributyl ammonium chloride (0.005 mole). The apparatus was flushed with air for 5 minutes and the solution was then heated to 80° C. for 5 hours. The progress of the reaction was followed from disappearance of the GMA. Gas chromatographic analysis of the reaction mixture indicated 95% reaction. The solution was cooled and dissolved in 250 ml. methylene chloride and washed three times with lN sodium hydroxide (100 ml.) and then with water until the washings were neutral. The organic layer was dried over magnesium sulfate and the solvent was removed at reduced pressure using a Rotovap. The oily residue was dried under high vacuum for 30 minutes. The yield was 133 g. (86%) product. H-1 NMR showed signals typical of GMA except the signal for the protons that were attached to the epoxide carbon at 2.8 and 3.3 ppm showed up as doublets and a quintet respectively. The spectrum also showed signals for the 4-dimethoxymethylphenyl group at ppms 7.8-6.9 and 3.4. 4-neck flask fitted with a mechanical stirrer thermometer, condenser and a vented nitrogen bubbler were placed The apparatus was flushed with air for 5 minutes 95% reaction The solution was cooled dissolved in 250 ml methylene chloride and washed three times with lN sodium hydroxide (100 ml.) The organic layer was dried over magnesium sulfate the solvent was removed at reduced pressure The oily residue was dried under high vacuum for 30 minutes

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

Procedure: A mixture of 4.88 g (40 mmol) of 4-hydroxybenzaldehyde, 6.6 g (206 mmol) of methanol and 5.1 g (48 mmol) of trimethylorthoformate and 28 mg of p-toluene sulfonic acid was stirred at room temperature for 12 h. An excess of NaHCO3 was then added and the mixture stirred for a further 60 h. The mixture was then filtered, the solvent removed in-vacuo and the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes) to give the title compound as a viscous oil. the mixture stirred for a further 60 h The mixture was then filtered the solvent removed in-vacuo the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes)

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