tert-butyl 2-hydroxybenzoate

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

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 tert-butyl salicylate (2.01 g, 10.3 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (2.69 g, 10.4 mmol) and cesium carbonate (4.05 g, 12.4 mmol) in dimethylformamide (20 mL) was stirred at room temperture overnight. The reaction mixture was partitioned between ethyl acetetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated in vacuo. The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%) and gave the subtitle compound (2.3 g, 89%). The reaction mixture was partitioned between ethyl acetetate and water The organic layer was dried over sodium sulphate, Na2SO4 filtered concentrated in vacuo The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%)

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

Procedure: A mixture of tert-butyl salicylate (2.01 g, 10.3 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (2.69 g, 10.4 mmol) and cesium carbonate (4.05 g, 12.4 mmol) in dimethylformamide (20 mL) was stirred at room temperture overnight. The reaction mixture was partitioned between ethyl acetetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated in vacuo. The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%) and gave the subtitle compound (2.3 g, 89%). The reaction mixture was partitioned between ethyl acetetate and water The organic layer was dried over sodium sulphate, Na2SO4 filtered concentrated in vacuo The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%)

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

Procedure: A mixture of tert-butyl salicylate (2.01 g, 10.3 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (2.69 g, 10.4 mmol) and cesium carbonate (4.05 g, 12.4 mmol) in dimethylformamide (20 mL) was stirred at room temperture overnight. The reaction mixture was partitioned between ethyl acetetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated in vacuo. The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%) and gave the subtitle compound (2.3 g, 89%). The reaction mixture was partitioned between ethyl acetetate and water The organic layer was dried over sodium sulphate, Na2SO4 filtered concentrated in vacuo The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: CDI (2.40 g, 14.79 mmol) was added to a solution of salicylic acid (2.02 g, 14.62 mmol) in DMF (20 mL). The reaction mixture was stirred at 50° C. for 30 min and tert-butyl alcohol (2.80 mL, 29.84 mmol) and DBU (4.4 mL, 29.45 mmol) were dropwise added. The reaction mixture was stirred at 50° C. for 16 h and allowed to reach r.t. It was poured into NaHCO3 (100 mL, saturated aqueous solution) and extracted with EtOAc (70 mL). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5% EtOAc/hexanes) to furnish 2.089 g of tert-butyl 2-hydroxybenzoate (colourless oil, yield: 73%). The reaction mixture was stirred at 50° C. for 16 h to reach r.t extracted with EtOAc (70 mL) The organic layer was dried over Na2SO4 (anhydrous) filtered concentrated chromatographed on SiO2 (5% EtOAc/hexanes)

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

Procedure: A mixture of tert-butyl salicylate (2.01 g, 10.3 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (2.69 g, 10.4 mmol) and cesium carbonate (4.05 g, 12.4 mmol) in dimethylformamide (20 mL) was stirred at room temperture overnight. The reaction mixture was partitioned between ethyl acetetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated in vacuo. The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%) and gave the subtitle compound (2.3 g, 89%). The reaction mixture was partitioned between ethyl acetetate and water The organic layer was dried over sodium sulphate, Na2SO4 filtered concentrated in vacuo The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%)