3-(3,4-dimethoxyphenyl)propanal

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

Procedure: A solution of 2.0 g (10.2 mmol) of the aldehyde prepared in step A in 40 ml CH2Cl2 is oxidised in the dark by the addition of 4.32 g (10.2 mmol) Dess-Marin periodinane. The reaction is complete after 30 minutes. The suspension formed is taken up into 50 ml CH2Cl2 and washed twice with sodium bicarbonate and 20% sodium thiosulphate solution. Concentration of the organic layer affords a beige crude product which is purified by chromatography hexane/ethyl acetate) to yield a yellow oil. The suspension formed washed twice with sodium bicarbonate and 20% sodium thiosulphate solution

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

Procedure: A solution of 2.0 g (10.2 mmol) of the aldehyde prepared in step A in 40 ml CH2Cl2 is oxidised in the dark by the addition of 4.32 g (10.2 mmol) Dess-Marin periodinane. The reaction is complete after 30 minutes. The suspension formed is taken up into 50 ml CH2Cl2 and washed twice with sodium bicarbonate and 20% sodium thiosulphate solution. Concentration of the organic layer affords a beige crude product which is purified by chromatography (hexane/ethyl acetate) to yield a yellow oil. The suspension formed washed twice with sodium bicarbonate and 20% sodium thiosulphate solution

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

Procedure: A solution of 2.0 g (10.2 mmol) of the aldehyde prepared in step A in 40 ml CH2Cl2 is oxidised in the dark by the addition of 4.32 g (10.2 mmol) Dess-Marin periodinane. The reaction is complete after 30 minutes. The suspension formed is taken up into 50 ml CH2Cl2 and washed twice with sodium bicarbonate and 20% sodium thiosulphate solution. Concentration of the organic layer affords a beige crude product which is purified by chromatography (hexane/ethyl acetate) to yield a yellow oil. The suspension formed washed twice with sodium bicarbonate and 20% sodium thiosulphate solution

Conditions: temp:-45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of oxalyl chloride(0.67 ml) in dichloromethane (80 ml) was added dropwise a solution of DMSO (1.18 ml) in dichloromethane(5 ml) at −78° C. To the mixture was added a solution of 1-(3,4-dimethoxyphenyl)propanol (1.50 g) in dichloromethane(25 ml) after 15 minutes. The mixture was stirred for an hour at −78° C. and for another hour at −45° C., then triethylamine(3.52 ml) was added. After stirring 20 minutes at 0° C., the mixture was quenched by a saturated aqueous NH4Cl solution, and extracted with dichloromethane. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:7 to 1:1) to give 3,4-dimethoxy-hydrocinnamaldehyde (1.05 g, 70.7%). After stirring 20 minutes at 0° C. the mixture was quenched by a saturated aqueous NH4Cl solution extracted with dichloromethane The organic layer was dried over MgSO4 evaporated in vacuo The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:7 to 1:1)

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

Procedure: A solution of 2.0 g (10.2 mmol) of the aldehyde prepared in step A in 40 ml CH2Cl2 is oxidised in the dark by the addition of 4.32 g (10.2 mmol) Dess-Marin periodinane. The reaction is complete after 30 minutes. The suspension formed is taken up into 50 ml CH2Cl2 and washed twice with sodium bicarbonate and 20% sodium thiosulphate solution. Concentration of the organic layer affords a beige crude product which is purified by chromatography hexane/ethyl acetate) to yield a yellow oil. The suspension formed washed twice with sodium bicarbonate and 20% sodium thiosulphate solution

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

Procedure: A solution of 2.0 g (10.2 mmol) of the aldehyde prepared in step A in 40 ml CH2Cl2 is oxidised in the dark by the addition of 4.32 g (10.2 mmol) Dess-Marin periodinane. The reaction is complete after 30 minutes. The suspension formed is taken up into 50 ml CH2Cl2 and washed twice with sodium bicarbonate and 20% sodium thiosulphate solution. Concentration of the organic layer affords a beige crude product which is purified by chromatography (hexane/ethyl acetate) to yield a yellow oil. The suspension formed washed twice with sodium bicarbonate and 20% sodium thiosulphate solution