3-(4-methylphenyl)propanal

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

Procedure: A solution of triphenylphosphine (0.117 moles, 30.8 g) in acetone (200 ml) is added under a nitrogen stream at r.t. with Cu (I) bis-(triphenyl-phosphine)-tetrahydroborate (0.067 moles, 40.69 g), then 3-(4-methylphenyl)propanoyl chloride (0.055 moles, 10 g) dissolved in acetone (85 ml) is dropped in 45'. The mixture is stirred at r.t. under nitrogen for 1 h. The precipitated solid is filtered, washing with acetone and the filtrate is evaporated under vacuum. The residue is dissolved in chloroform (340 ml), added with cuprous chloride (0.135 moles, 13.38 g) and stirred under nitrogen stream for 1 h at r.t. The mixture is filtered through celite, the filtrate is evaporated to dryness and the resulting residue is taken up into ethyl ether and petroleum ether, filtered and evaporated under vacuum to obtain an oil. Yield: 6.7 g (83%) is dropped in 45' The precipitated solid is filtered washing with acetone the filtrate is evaporated under vacuum The residue is dissolved in chloroform (340 ml) stirred under nitrogen stream for 1 h at r.t The mixture is filtered through celite the filtrate is evaporated to dryness filtered evaporated under vacuum to obtain an oil

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

Procedure: Prepared according to the previously described general procedure (GP11) by reaction of 2-(2,4-dimethyl-imidazol-1-yl)-ethylamine with 3-p-tolyl-propionaldehyde. LC-MS: tR=0.57 min.; [M+H]+=270 g/mol. Prepared

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

Procedure: 4-Methyl cyclohexanepropanal was similarly prepared as described in Examples I and II. First, 4-methyl benzaldehyde (140 g, commercially available from Mitsubishi Gas Chemical America, Inc.) was used to obtain 3-(4-methyl-phenyl)-propionaldehyde (130 g) with a boiling point of 120° C. at a pressure of 21 mmHg 3-(4-Methyl-phenyl)-propionaldehyde (180 g) was consequently used to provide 4-methyl cyclohexanepropanal (104 g) with a boiling point of 112° C. at a pressure of 24 mmHg

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

Procedure: 4-Methyl 1-(3-methoxy-2-propen-1-yl)benzene was similarly prepared as described in Examples I and II. First, 4-methyl benzaldehyde (140 g, commercially available from Mitsubishi Gas Chemical Company, Inc.) was used to obtain 3-(4-methyl-phenyl)-propionaldehyde (130 g) with a boiling point of 120° C. at a pressure of 21 mmHg. 3-(4-Methyl-phenyl)-propionaldehyde (225 g) was consequently used to provide 4-methyl 1-(3-methoxy-2-propen-1-yl)benzene (139 g) with a boiling point of 117° C. at a pressure of 35 mmHg

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

Procedure: 4-Methyl cyclohexanepropanal was similarly prepared as described in Examples I and II. First, 4-methyl benzaldehyde (140 g, commercially available from Mitsubishi Gas Chemical Company, Inc.) was used to obtain 3-(4-methyl-phenyl)-propionaldehyde (130 g) with a boiling point of 120° C. at a pressure of 21 mmHg. 3-(4-Methyl-phenyl)-propionaldehyde (180 g) was consequently used to provide 4-methyl cyclohexanepropanal (104 g) with a boiling point of 112° C. at a pressure of 24 mmHg.