2,3-dimethoxycyclohexa-2,5-diene-1,4-dione

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

Procedure: Sodium hydrosulphite (Na2S2O4, 26 g) was added portionwise to a stirred solution of 2,3-dimethoxy-1,4-benzoquinone (J. Med. Chem., 1971, 14, 45; 5 g) in a mixture of methanol (50 ml) and water (100 ml). The resultant mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give 2,3-dimethoxyhydroquinone (2 g); NMR Spectrum: (CD3SOCD3) 3.71 (s, 6H), 6.37 (s, 2H), 8.47 (s, 2H). The mixture was partitioned between ethyl acetate and water The organic phase was dried (MgSO4) evaporated

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

Procedure: Sodium hydrosulphite (Na2S2O4, 26 g) was added portionwise to a stirred solution of 2,3-dimethoxy-1,4-benzoquinone (J. Med. Chem., 1971, 14, 45; 5 g) in a mixture of methanol (50 ml) and water (100 ml). The resultant mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give 2,3-dimethoxyhydroquinone (2 g); NMR Spectrum: (CD3SOCD3) 3.71 (s, 6H), 6.37 (s, 2H), 8.47 (s, 2H). The mixture was partitioned between ethyl acetate and water The organic phase was dried (MgSO4) evaporated

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

Procedure: A benzene (8 ml) solution of 2,3-dimethoxybenzo-1,4-quinone (1.0 g, 5.9 mmol) and 3-chloro-1-methoxy-1,3-butadiene (1.4 g, 12.0 mmol) is stirred for 30 hours under an inert atmosphere. After this time, the reaction mixture is concentrated and then dissolved in pyridine (8 ml). Acetic anhydride (3.0 g) is added, and the solution is stirred for 12 hours under an inert atmosphere. The contents are diluted ten-fold with water and extracted with ethyl acetate. The organics are then washed with water, brine, and then dried over sodium sulfate. Concentration, followed by flash chromatography (hexane/ethyl acetate 3:1) affords 2.03 g (93%) of a compound of the formula ##STR5## After this time, the reaction mixture is concentrated dissolved in pyridine (8 ml) Acetic anhydride (3.0 g) is added The contents are diluted ten-fold with water extracted with ethyl acetate The organics are then washed with water, brine dried over sodium sulfate Concentration

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

Procedure: A dichloromethane (10 ml) solution of 2,3-dimethoxybenzo-1,4-quinone (1.0 g, 5.9 mmol) and 3-chloro-1-methoxy-1,3-butadiene (1.4 g, 12.0 mmol) is stirred for 24 hours at room temperature under an inert atmosphere. After this time, 80 mg of d,1-camphorsulfonic acid is added and the solution is stirred an additional 12 hours. The mixture is then concentrated and subsequently dissolved in pyridine (15 ml) and acetic anhydride (3.0 g). After stirring for five hours under an inert atmosphere, the solution is concentrated to dryness and taken up in dichloromethane. The organics are washed with water, brine, and then dried (sodium sulfate) and concentrated to afford 1.17 g (58%) of pure 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene. The mixture is then concentrated subsequently dissolved in pyridine (15 ml) After stirring for five hours under an inert atmosphere the solution is concentrated to dryness The organics are washed with water, brine dried (sodium sulfate) concentrated

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

Procedure: A benzene (8 ml) solution of 2,3-dimethoxybenzo-1,4-quinone (1.0 g, 5.9 mmol) and 3-chloro-1-methoxy-1,3-butadiene (1.4 g, 12.0 mmol) is stirred for 35 hours under an inert atmosphere. After this time, oxygen or air is briefly bubbled through the solution (20 minutes) and the contents are passed through a silica gel plug to afford 1.07 g (72%) of analytically pure 2,3-dimethoxy-6-chloro-1,4-naphthoquinone, mp 127°-130° C. After this time, oxygen or air is briefly bubbled through the solution (20 minutes)

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

Procedure: Sodium hydrosulphite (Na2S2O4, 26 g) was added portionwise to a stirred solution of 2,3-dimethoxy-1,4-benzoquinone (J. Med. Chem., 1971, 14, 45; 5 g) in a mixture of methanol (50 ml) and water (100 ml). The resultant mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give 2,3-dimethoxyhydroquinone (2 g); NMR Spectrum: (CD3SOCD3) 3.71 (s, 6H), 6.37 (s, 2H), 8.47 (s, 2H). The mixture was partitioned between ethyl acetate and water The organic phase was dried (MgSO4) evaporated

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

Procedure: Sodium hydrosulphite (Na2S2O4, 26 g) was added portionwise to a stirred solution of 2,3-dimethoxy-1,4-benzoquinone (J. Med. Chem., 1971, 14, 45; 5 g) in a mixture of methanol (50 ml) and water (100 ml). The resultant mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give 2,3-dimethoxyhydroquinone (2 g); NMR Spectrum: (CD3SOCD3) 3.71 (s, 6H), 6.37 (s, 2H), 8.47 (s, 2H). The mixture was partitioned between ethyl acetate and water The organic phase was dried (MgSO4) evaporated