3,4-dichlorobenzene-1,2-diol

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 11.0 g of 3,4-dichloro-1,2-benzenediol, 15.38 g of potassium carbonate, 27 g of ethyl dibromoacetate and 100 ml of dimethylformamide is stirred at 100° C. under argon gas atmosphere for 4 hours. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue. The organic layer is separated, washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 10.75 g of ethyl 4,5-dichloro-1,3-benzodioxole-2carboxylate. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue The organic layer is separated washed with water dried evaporated to remove solvent The residue is purified by silica gel column chromatography

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

Procedure: A suspension of 104 g of 3,4-dichloro-1,2benzenediol, 240 g of potassium carbonate and 354 g of methyl iodide in 2 litters of acetone is refluxed for 2 hours. The reaction mixture is filtered and washed with acetone. The filtrate and the washings are combined and evaporated to remove solvent. Water is added to the residue and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is distilled under reduced pressure to give 110.5 g of 1,2-dichloro-3,4-dimethoxybenzene. The reaction mixture is filtered washed with acetone evaporated to remove solvent Water is added to the residue the mixture is extracted with ethyl acetate The extract is washed with water dried evaporated to remove solvent The residue is distilled under reduced pressure

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

Procedure: A suspension of 104 g of 3,4-dichloro-1,2benzenediol, 240 g of potassium carbonate and 354 g of methyl iodide in 2 litters of acetone is refluxed for 2 hours. The reaction mixture is filtered and washed with acetone. The filtrate and the washings are combined and evaporated to remove solvent. Water is added to the residue and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is distilled under reduced pressure to give 110.5 g of 1,2-dichloro-3,4-dimethoxybenzene. The reaction mixture is filtered washed with acetone evaporated to remove solvent Water is added to the residue the mixture is extracted with ethyl acetate The extract is washed with water dried evaporated to remove solvent The residue is distilled under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 11.0 g of 3,4-dichloro-1,2-benzenediol, 15.38 g of potassium carbonate, 27 g of ethyl dibromoacetate and 100 ml of dimethylformamide is stirred at 100° C. under argon gas atmosphere for 4 hours. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue. The organic layer is separated, washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 10.75 g of ethyl 4,5-dichloro-1,3-benzodioxole-2-carboxylate. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue The organic layer is separated washed with water dried evaporated to remove solvent The residue is purified by silica gel column chromatography

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

Procedure: A suspension of 104 g of 3,4-dichloro-1,2-benzenediol, 240 g of potassium carbonate and 354 g of methyl iodide in 2 litters of acetone is refluxed for 2 hours. The reaction mixture is filtered and washed with acetone. The filtrate and the washings are combined and evaporated to remove solvent. Water is added to the residue and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is distilled under reduced pressure to give 110.5 g of 1,2-dichloro-3,4-dimethoxybenzene. The reaction mixture is filtered washed with acetone evaporated to remove solvent Water is added to the residue the mixture is extracted with ethyl acetate The extract is washed with water dried evaporated to remove solvent The residue is distilled under reduced pressure

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

Procedure: In 250 ml of dimethylformamide is dissolved 8.95 g of the compound (II), and 4.80 g (2 equivalent) of 50% sodium hydride oily suspension and 10.25 g (1.3 equivalent) of benzyl bromide are added thereto. The mixture is stirred for 10 minutes under ice cooling, then poured into 200 ml of water, and sparingly soluble crystals are collected by filtration and recrystallized from hexane to give 2.096 g of 1,2-dibenzyloxy-2-hydroxy-3,4-dichlorobenzene, mp. 74°-75° C. are added are collected by filtration recrystallized from hexane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 11.0 g of 3,4-dichloro-1,2-benzenediol, 15.38 g of potassium carbonate, 27 g of ethyl dibromoacetate and 100 ml of dimethylformamide is stirred at 100° C. under argon gas atmosphere for 4 hours. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue. The organic layer is separated, washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 10.75 g of ethyl 4,5-dichloro-1,3-benzodioxole-2carboxylate. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue The organic layer is separated washed with water dried evaporated to remove solvent The residue is purified by silica gel column chromatography

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

Procedure: A suspension of 104 g of 3,4-dichloro-1,2benzenediol, 240 g of potassium carbonate and 354 g of methyl iodide in 2 litters of acetone is refluxed for 2 hours. The reaction mixture is filtered and washed with acetone. The filtrate and the washings are combined and evaporated to remove solvent. Water is added to the residue and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is distilled under reduced pressure to give 110.5 g of 1,2-dichloro-3,4-dimethoxybenzene. The reaction mixture is filtered washed with acetone evaporated to remove solvent Water is added to the residue the mixture is extracted with ethyl acetate The extract is washed with water dried evaporated to remove solvent The residue is distilled under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 11.0 g of 3,4-dichloro-1,2-benzenediol, 15.38 g of potassium carbonate, 27 g of ethyl dibromoacetate and 100 ml of dimethylformamide is stirred at 100° C. under argon gas atmosphere for 4 hours. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue. The organic layer is separated, washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 10.75 g of ethyl 4,5-dichloro-1,3-benzodioxole-2-carboxylate. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue The organic layer is separated washed with water dried evaporated to remove solvent The residue is purified by silica gel column chromatography

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

Procedure: A suspension of 104 g of 3,4-dichloro-1,2-benzenediol, 240 g of potassium carbonate and 354 g of methyl iodide in 2 litters of acetone is refluxed for 2 hours. The reaction mixture is filtered and washed with acetone. The filtrate and the washings are combined and evaporated to remove solvent. Water is added to the residue and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is distilled under reduced pressure to give 110.5 g of 1,2-dichloro-3,4-dimethoxybenzene. The reaction mixture is filtered washed with acetone evaporated to remove solvent Water is added to the residue the mixture is extracted with ethyl acetate The extract is washed with water dried evaporated to remove solvent The residue is distilled under reduced pressure