ethyl (E)-3-(4-chlorophenyl)prop-2-enoate

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

Procedure: To a solution of trans-4-chlorocinnamic acid (10 g, 55 mmol) in ethanol (60 mL) was added a catalytic amount of concentrated sulfuric acid (2-3 drops), and the mixture was heated (70° C.) until a majority of the starting material was consumed as evidenced by LCMS. The reaction mixture was concentrated and the contents were redissolved in ethyl acetate. The organic phase was extracted with an aqueous solution of sodium bicarbonate (5%, 3×) followed by a brine wash. The organic phase was dried (MgSO4), filtered and concentrated to afford trans-4-chlorocinnamic acid ethyl ester as a colorless oil. MS (ESI) m/z 211.1 ([M+H]+). was consumed The reaction mixture was concentrated the contents were redissolved in ethyl acetate The organic phase was extracted with an aqueous solution of sodium bicarbonate (5%, 3×) wash The organic phase was dried (MgSO4) filtered concentrated

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

Procedure: To a solution of trans-4-chlorocinnamic acid (10 g, 55 mmol) in ethanol (60 mL) was added a catalytic amount of concentrated sulfuric acid (2-3 drops), and the mixture was heated (70° C.) until a majority of the starting material was consumed as evidenced by LCMS. The reaction mixture was concentrated and the contents were redissolved in ethyl acetate. The organic phase was extracted with an aqueous solution of sodium bicarbonate (5%, 3×) followed by a brine wash. The organic phase was dried (MgSO4), filtered and concentrated to afford trans-4-chlorocinnamic acid ethyl ester as a colorless oil. MS (ESI) m/z 211.1 ([M+H]+). was consumed The reaction mixture was concentrated the contents were redissolved in ethyl acetate The organic phase was extracted with an aqueous solution of sodium bicarbonate (5%, 3×) wash The organic phase was dried (MgSO4) filtered concentrated

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

Procedure: To a solution of (E)-3-(4-chloro-phenyl)-acrylic acid ethyl ester (0.37 g, 1.73 mmol) in ethyl acetate (10 ml) were added palladium on activated charcoal (18 mg) and zinc bromide (80 mg, 0.35 mmol). The reaction vessel was then pressurized with hydrogen gas to a pressure of 1 atmosphere and the mixture was stirred for 18 h. The catalyst was then removed by filtration, washing with ethyl acetate, and the filtrate was concentrated in vacuo to yield a colourless oil which was used for the next step without further purification; MS (ISP): 214.2, 212.1 ([M+H]+.). The catalyst was then removed by filtration washing with ethyl acetate the filtrate was concentrated in vacuo to yield a colourless oil which was used for the next step without further purification