[3-[8-(1,3-dioxolan-2-yl)octoxy]-4-methylphenyl]methanol

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

Procedure: To a stirred solution of 5-(hydroxymethyl)-2-methylphenol (0.57 g, 4.15 mmol) in dimethyl formamide (15 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (1.00 g, 3.77 mmol) and potassium carbonate (0.63 g, 4.57 mmol), and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (0.5 g, 41%). The reaction mixture was cooled to room temperature extracted with ethyl acetate (×3) The combined organic extracts were washed with brine dried (magnesium sulphate) filtered concentrated under reduced pressure The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane

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

Procedure: To a stirred solution of 5-(hydroxymethyl)-2-methylphenol (0.57 g, 4.15 mmol) in dimethyl formamide (15 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (1.00 g, 3.77 mmol) and potassium carbonate (0.63 g, 4.57 mmol), and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (0.5 g, 41%). The reaction mixture was cooled to room temperature extracted with ethyl acetate (×3) The combined organic extracts were washed with brine dried (magnesium sulphate) filtered concentrated under reduced pressure The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane

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

Procedure: To a stirred solution of 5-(hydroxymethyl)-2-methylphenol (0.57 g, 4.15 mmol) in dimethyl formamide (15 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (1.00 g, 3.77 mmol) and potassium carbonate (0.63 g, 4.57 mmol), and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (0.5 g, 41%). The reaction mixture was cooled to room temperature extracted with ethyl acetate (×3) The combined organic extracts were washed with brine dried (magnesium sulphate) filtered concentrated under reduced pressure The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane

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

Procedure: To a stirred solution of 5-(hydroxymethyl)-2-methylphenol (0.57 g, 4.15 mmol) in dimethyl formamide (15 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (1.00 g, 3.77 mmol) and potassium carbonate (0.63 g, 4.57 mmol), and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (0.5 g, 41%). The reaction mixture was cooled to room temperature extracted with ethyl acetate (×3) The combined organic extracts were washed with brine dried (magnesium sulphate) filtered concentrated under reduced pressure The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane