ethyl 2-(4-hydroxyphenyl)propanoate

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

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

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

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

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

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

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

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

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 13.0 g (78.2 mmol) of 2-(4-hydroxyphenyl)propionic acid in 250 ml EtOH 5.82 ml (78.2 mmol) thionyl chloride are added slowly at 0° C. The reaction mixture is stirred at 70° C. for 2 h. After cooling to r.t. the solvent is removed in vacuo. The residue is mixed with toluene and the solvent is removed again. are added slowly at 0° C After cooling to r.t. the solvent is removed in vacuo The residue is mixed with toluene the solvent is removed again

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

Procedure: A solution of 2-(4-hydroxy-phenyl)-propionic acid ethyl ester (9.02 g) in acetic acid (75 mL) was added nitric acid (60%, 5.24 g in AcOH) at room temperature. The reaction mixture was stirred for 30 minutes at room temperature and added water. The mixture was extracted with EtOAc and the organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1) to afford the product as yellow oil. (9.71 g) The mixture was extracted with EtOAc the organic layer was dried over magnesium sulfate filtered concentrated in vacuo The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1)

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

Procedure: A solution of 2-(4-hydroxy-phenyl)-propionic acid ethyl ester (9.02 g) in acetic acid (75 mL) was added nitric acid (60%, 5.24 g in AcOH) at room temperature. The reaction mixture was stirred for 30 minutes at room temperature and added water. The mixture was extracted with EtOAc and the organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1) to afford the product as yellow oil. (9.71 g) The mixture was extracted with EtOAc the organic layer was dried over magnesium sulfate filtered concentrated in vacuo The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1)

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

Procedure: Ethyl 2-(4-hydroxyphenyl)propanoate (275 mg, 1.42 mmol) in acetic acid (2 mL) was added nitric acid (60-62%, 300 mg, 2.86 mmol) at room temperature. The mixture was stirred for 1 hour at 50° C. and cooled to room temperature. The reaction mixture was poured into ice water (20 mL) and extracted with EtOAc. The organic layer was dried with MgSO4 and filtered. EtOAc was removed by evaporation. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=6/1. cooled to room temperature extracted with EtOAc The organic layer was dried with MgSO4 filtered EtOAc was removed by evaporation The residue was purified by column chromatography eluting with n-Hexane/EtOAc=6/1