[2,3,5,6-tetrafluoro-4-(hydroxymethyl)phenyl]methanol

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,3,5,6-Tetrafluoro-1,4-benzene dimethanol (1 g; 4.8 m.mol) was added to hydrochloric acid 36°Tw (10 ml; 115 m.mol) at 20° C., followed by toluene (10 ml). The mixture was then stirred and warmed to 90° C. and maintained at this temperature for 7 hours to complete the reaction. maintained at this temperature for 7 hours the reaction

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,3,5,6-Tetrafluoro-1,4-benzene dimethanol (1 g; 4.8 m.mol) was added to hydrochloric acid 36°Tw (10 ml; 115 m.mol) at 20° C., followed by toluene (10 ml). The mixture was then stirred and warmed to 90° C. and maintained at this temperature for 7 hours to complete the reaction. maintained at this temperature for 7 hours the reaction

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,3,5,6-Tetrafluoro-1,4-benzene dimethanol (1 g; 4.8 m.mol) was added to hydrochloric acid 36°Tw (10 ml; 115 m.mol) at 20° C., followed by toluene (10 ml). The mixture was then stirred and warmed to 90° C. and maintained at this temperature for 7 hours to complete the reaction. maintained at this temperature for 7 hours the reaction

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

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reaction vessel that was charged nitrogen, 5.00 g (23.1 mmol) of 2,3,5,6-tetrafluoro-1,4-benzenedimethanol, 15.00 g of water and 6.85 g (46.3 mmol) of 27% aqueous sodium hydroxide solution were charged subsequently, and heated to 65° C. with stirring. The starting compound was completely dissolved to be clear solution. Then, the reaction mixture was allowed to cool to room temperature with stirring. At this time, some precipitate was observed. To the reaction mixture, 20.0 g of toluene was added and then 4.33 g (32.6 mmol) of dimethyl sulfate was added dropwise over 7.5 hours at room temperature. After the addition, the pH of the aqueous layer became 13.5. The layers of the reaction mixture were separated, and the pH of the aqueous layer was adjusted to about 3 by adding 10% sulfric acid. The aqueous layer was extracted with 30 ml of ethyl acetate, and the combined organic layers were washed- with 30 ml of water, concentrated, and dried under a reduced pressure to give 5.22 g of crude 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol. The crude 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol was subjected to content analysis by GC internal standard method (Analytical method 1 given later). GC area percentage of the crude product: 85% of the objective compound, 1% of the starting compound and 13% of the by-product compound Content analysis by GC internal standard method: 85% of the objective compound and 86% of the yield of pure compound were charged subsequently The starting compound was completely dissolved to cool to room temperature with stirring After the addition The layers of the reaction mixture were separated by adding 10% sulfric acid The aqueous layer was extracted with 30 ml of ethyl acetate concentrated dried under a reduced pressure

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reaction vessel that was charged nitrogen, 5.00 g (23.1 mmol) of 2,3,5,6-tetrafluoro-1,4-benzenedimethanol, 15.00 g of water and 1.30 g (23.1 mmol) of potassium hydroxide were charged subsequently, and heated to 60° C. with stirring. At this time, solid 2,3,5,6-tetrafluoro-1,4-benzenedimethanol was completely dissolved to be a clear solution. Then, a mixture of 15.0 g of toluene and 3.07 g (23.1 mmol) of dimethyl sulfate was added at 55±5° C. After stirring at 50±5° C. for 1.5 hours, 0.64 g (11.4 mmol) of potassium hydroxide and 1.51 g (12.6 mmol) of dimethyl sulfate were added. After 1.5 hours, 0.66 g (11.7 mmol) of potassium hydroxide and 1.51 g (12.6 mmol) of dimethyl sulfate were further added and stirred at the same temperature for 1.5 hours. Allowing the reaction mixture to cool to room temperature, the layers of the reaction mixture were separated and the water layer was extracted with 30 ml of ethyl acetate. The organic layers were combined, washed with 30 ml of water, concentrated, and dried under reduced pressure to give 5.22 g of crude 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol. The crude 4-methoxymethyl-2,3,5,6-tetrafluorobenzenemethanol was subjected to content analysis by GC internal standard method (Analytical method 1 given later). GC area percentage of the crude product: 87% of the objective compound, 4% of the starting compound and 8% of the by-product compound Content analysis by GC internal standard method: 85% of the objective compound and 86% of the yield of pure compound were charged subsequently was added at 55±5° C After stirring at 50±5° C. for 1.5 hours stirred at the same temperature for 1.5 hours Allowing the reaction mixture to cool to room temperature the layers of the reaction mixture were separated the water layer was extracted with 30 ml of ethyl acetate washed with 30 ml of water concentrated dried under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,3,5,6-Tetrafluoro-1,4-benzene dimethanol (1 g; 4.8 m.mol) was added to hydrochloric acid 36°Tw (10 ml; 115 m.mol) at 20° C., followed by toluene (10 ml). The mixture was then stirred and warmed to 90° C. and maintained at this temperature for 7 hours to complete the reaction. maintained at this temperature for 7 hours the reaction