4-(2-hydroxyethoxy)-3-methoxybenzaldehyde

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

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

Procedure: Vanillin (15.2 g, 0.01 m), water (70 mL), and sodium hydroxide (5.0 g, 0.0125 m) are mixed and stirred for a few minutes until solution is completed. 2-Chloroethanol (9.7 g, 0.012 m) is added and the reaction mixture heated at reflux for 16 hours and then cooled. The solid product is collected by filtration, washed with water, dried, and finally recrystallized from toluene. The yield is 13.0 g (69.9% of the theoretical yield). the reaction mixture heated at reflux for 16 hours cooled The solid product is collected by filtration washed with water dried finally recrystallized from toluene The yield is 13.0 g (69.9% of the theoretical yield)

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

Procedure: Vanillin (15.2 g, 0.01 m), water (70 mL), and sodium hydroxide (5.0 g, 0.0125 m) are mixed and stirred for a few minutes until solution is completed. 2-Chloroethanol (9.7 g, 0.012 m) is added and the reaction mixture heated at reflux for 16 hours and then cooled. The solid product is collected by filtration, washed with water, dried, and finally recrystallized from toluene. The yield is 13.0 g (69.9% of the theoretical yield). the reaction mixture heated at reflux for 16 hours cooled The solid product is collected by filtration washed with water dried finally recrystallized from toluene The yield is 13.0 g (69.9% of the theoretical yield)

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

Procedure: 25.9 g (170 mmol) vanillin (Aldrich), 33.3 g (266 mmol) 2-bromoethanol (Aldrich), 35.2 g (255 mmol) potassium carbonate (Sigma-Aldrich), and 20 g molecular sieves (Aldrich) were combined in a 1 liter round bottom flask equipped with magnetic stirrer and nitrogen inlet. Acetone (600 ml) (Chromesolv for HPLC, >99.9%, Sigma-Aldrich) was added and the reaction mixture was refluxed for 16 hours using an external glycerol heating bath set to 65° C. The solids were filtered and the solvent was removed via rotary evaporation to yield a yellow oil. White crystals were obtained by recrystallization in ethyl alcohol at −20° C. (40% yield). equipped with magnetic stirrer and nitrogen inlet the reaction mixture was refluxed for 16 hours set to 65° C The solids were filtered the solvent was removed via rotary evaporation to yield a yellow oil

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

Procedure: Vanillin (15.2 g, 0.01 m), water (70 mL), and sodium hydroxide (5.0 g, 0.0125 m) are mixed and stirred for a few minutes until solution is completed. 2-Chloroethanol (9.7 g, 0.012 m) is added and the reaction mixture heated at reflux for 16 hours and then cooled. The solid product is collected by filtration, washed with water, dried, and finally recrystallized from toluene. The yield is 13.0 g (69.9% of the theoretical yield). the reaction mixture heated at reflux for 16 hours cooled The solid product is collected by filtration washed with water dried finally recrystallized from toluene The yield is 13.0 g (69.9% of the theoretical yield)

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

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

Procedure: A mixture of 4-(2-hydroxyethoxy)-3-methoxybenzaldehyde (0.98 g, 0.005 mol), (see Example 1 of U.S. Pat. No. 4,707,537, supra), methylsulfonylacetonitrile (0.60 g, 0.005 m), ethanol (10 mL) and piperidine (5 drops) is heated at reflux for 1 hour, during which time the product crystallizes. The reaction mixture is allowed to cool and the very pale yellow product is collected by filtration, washed with ethanol and dried in air. The yield of product is 1.05 g (70.9%). Mass spectrometry supports the following structure: ##STR22## In methylene chloride the product has an absorption maximum at 362 nm. at reflux for 1 hour, during which time the product crystallizes to cool the very pale yellow product is collected by filtration washed with ethanol dried in air

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

Procedure: 25.9 g (170 mmol) vanillin (Aldrich), 33.3 g (266 mmol) 2-bromoethanol (Aldrich), 35.2 g (255 mmol) potassium carbonate (Sigma-Aldrich), and 20 g molecular sieves (Aldrich) were combined in a 1 liter round bottom flask equipped with magnetic stirrer and nitrogen inlet. Acetone (600 ml) (Chromasolv for HPLC, >99.9%, Sigma-Aldrich) was added and the reaction mixture was refluxed for 16 hours using an external glycerol heating bath set to 65° C. The solids were filtered and the solvent was removed via rotary evaporation to yield a yellow oil. White crystals were obtained by recrystallization in ethyl alcohol at −20° C. (40% yield). equipped with magnetic stirrer and nitrogen inlet the reaction mixture was refluxed for 16 hours set to 65° C The solids were filtered the solvent was removed via rotary evaporation to yield a yellow oil

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

Procedure: 25.9 g (170 mmol) vanillin (Aldrich), 33.3 g (266 mmol) 2-bromoethanol (Aldrich), 35.2 g (255 mmol) potassium carbonate (Sigma-Aldrich), and 20 g molecular sieves (Aldrich) were combined in a 1 liter round bottom flask equipped with magnetic stirrer and nitrogen inlet. Acetone (600 ml) (Chromesolv for HPLC, >99.9%, Sigma-Aldrich) was added and the reaction mixture was refluxed for 16 hours using an external glycerol heating bath set to 65° C. The solids were filtered and the solvent was removed via rotary evaporation to yield a yellow oil. White crystals were obtained by recrystallization in ethyl alcohol at −20° C. (40% yield). equipped with magnetic stirrer and nitrogen inlet the reaction mixture was refluxed for 16 hours set to 65° C The solids were filtered the solvent was removed via rotary evaporation to yield a yellow oil

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

Procedure: Vanillin (15.2 g, 0.01 m), water (70 mL), and sodium hydroxide (5.0 g, 0.0125 m) are mixed and stirred for a few minutes until solution is completed. 2-Chloroethanol (9.7 g, 0.012 m) is added and the reaction mixture heated at reflux for 16 hours and then cooled. The solid product is collected by filtration, washed with water, dried, and finally recrystallized from toluene. The yield is 13.0 g (69.9% of the theoretical yield). the reaction mixture heated at reflux for 16 hours cooled The solid product is collected by filtration washed with water dried finally recrystallized from toluene The yield is 13.0 g (69.9% of the theoretical yield)