2-(2,3-dichlorophenyl)acetaldehyde

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

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

Procedure: To a solution of 13.0 g (0.074 mole) of crude 2,3-dichlorobenzeneacetaldehyde in 50 ml of MeOH was added 5.7 ml (0.074 mole) of (S)-2-amino-1-propanol. The reaction was placed under an atmosphere of argon and 3.6 g (0.058 mole) of sodium cyanoborohydride was added. After stirring for 2.5 hr, the reaction was made acidic by adding ethereal hydrogen chloride. After stirring of 30 min enough 3N sodium hydroxide was added to make the reaction basic. The reaction mixture was extracted with ether and the ether layer was washed with water, brine and dried (K2CO3). Evaporation of the solvent in vacuo gave a yellow oil. The oil was treated with ethereal hydrogen chloride and the solid was collected. The solid was recrystallized from 2-propanol to give 5.10 g of the title compound (28% yield), mp 148°-151° C. was added The reaction mixture was extracted with ether the ether layer was washed with water, brine dried (K2CO3) Evaporation of the solvent in vacuo gave a yellow oil the solid was collected The solid was recrystallized from 2-propanol

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

Procedure: To a solution of 13.0 g (0.074 mole) of crude 2,3-dichlorobenzeneacetaldehyde in 50 ml of MeOH was added 5.7 ml (0.074 mole) of (S)-2-amino-1-propanol. The reaction was placed under an atmosphere of argon and 3.6 g (0.058 mole) of sodium cyanoborohydride was added. After stirring for 2.5 hr, the reaction was made acidic by adding ethereal hydrogen chloride. After stirring of 30 min enough 3N sodium hydroxide was added to make the reaction basic. The reaction mixture was extracted with ether and the ether layer was washed with water, brine and dried (K2CO3). Evaporation of the solvent in vacuo gave a yellow oil. The oil was treated with ethereal hydrogen chloride and the solid was collected. The solid was recrystallized from 2-propanol to give 5.10 g of the title compound (28% yield), mp 148°-151° C. was added The reaction mixture was extracted with ether the ether layer was washed with water, brine dried (K2CO3) Evaporation of the solvent in vacuo gave a yellow oil the solid was collected The solid was recrystallized from 2-propanol

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

Procedure: To a solution of 15.0 g (0.074 mole) 1,2-dichloro-3-(2-methoxyethenyl)benzene in 150 ml of THF was added 15 ml of 35% perchloric acid in water. The reaction was refluxed for 3.5 hr then poured into ice/water. The aqueous layer was extracted two times with ether, the organics were washed with water, brine and dried (MgSO4). Evaporation of the solvent gave 13.91 g of crude 2,3-dichlorobenzeneacetaldehyde a yellow oil (99%). The reaction was refluxed for 3.5 hr The aqueous layer was extracted two times with ether the organics were washed with water, brine dried (MgSO4) Evaporation of the solvent

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

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

Procedure: To a solution of 13.0 g (0.074 mole) of crude 2,3-dichlorobenzeneacetaldehyde in 50 ml of MeOH was added 5.7 ml (0.074 mole) of (S)-2-amino-1-propanol. The reaction was placed under an atmosphere of argon and 3.6 g (0.058 mole) of sodium cyanoborohydride was added. After stirring for 2.5 hr, the reaction was made acidic by adding ethereal hydrogen chloride. After stirring of 30 min enough 3N sodium hydroxide was added to make the reaction basic. The reaction mixture was extracted with ether and the ether layer was washed with water, brine and dried (K2CO3). Evaporation of the solvent in vacuo gave a yellow oil. The oil was treated with ethereal hydrogen chloride and the solid was collected. The solid was recrystallized from 2-propanol to give 5.10 g of the title compound (28% yield), mp 148°-151° C. was added The reaction mixture was extracted with ether the ether layer was washed with water, brine dried (K2CO3) Evaporation of the solvent in vacuo gave a yellow oil the solid was collected The solid was recrystallized from 2-propanol

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

Procedure: To a solution of 15.0 g (0.074 mole) 1,2-dichloro-3-(2-methoxyethenyl)benzene in 150 ml of THF was added 15 ml of 35% perchloric acid in water. The reaction was refluxed for 3.5 hr then poured into ice/water. The aqueous layer was extracted two times with ether, the organics were washed with water, brine and dried (MgSO4). Evaporation of the solvent gave 13.91 g of crude 2,3-dichlorobenzeneacetaldehyde a yellow oil (99%). The reaction was refluxed for 3.5 hr The aqueous layer was extracted two times with ether the organics were washed with water, brine dried (MgSO4) Evaporation of the solvent