ethyl 3,5-dihydroxybenzoate

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

Conditions: temp:120.01; pressure:0.00; stir:

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

Procedure: Using 1.5 g (9.55 mmol) of 3,4,5-trifluoro-benzonitrile and 3,5-dihydroxy-benzoic acid ethyl ester (1.73 g, 9.55 mmol) and following the procedure of Example 42(a) afforded 1.2 g of the required product. 1H NMR (DMSO-d6): δ 1.28 (3H, t), 4.27 (2H, q), 6.67 (1H, t), 6.92 (1H, s), 7.18 (1H, s), 8.08 (2H, d), 10.20 (1H, brs).

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

Procedure: Using 1.5 g (9.55 mmol) of 3,4,5-trifluoro-benzonitrile and 3,5-dihydroxy-benzoic acid ethyl ester (1.73 g, 9.55 mmol) and following the procedure of Example 42(a) afforded 1.2 g of the required product. 1H NMR (DMSO-d6): δ 1.28 (3H, t), 4.27 (2H, q), 6.67 (1H, t), 6.92 (1H, s), 7.18 (1H, s), 8.08 (2H, d), 10.20 (1H, brs).

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

Procedure: 3,5-Dihydroxy benzoic acid ethyl ester (1.45 g, 7.95 mmol) and 3-bromomethyl-benzonitrile (6.23 g, 31.8 mmol) and other reagents as described in Example 75(a) were used to afford 2.3 g of the required product. 1H NMR (DMSO-d6): 1.15 (3H, t), 4.15 (2H, q), 5.3 (4H, s), 7.0 (1H, s), 7.18 (2H, s), 7.64 (4H, d), 7.86 (4H, d).

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

Procedure: 3,5-Dihydroxy benzoic acid ethyl ester (1.45 g, 7.95 mmol) and 3-bromomethyl-benzonitrile (6.23 g, 31.8 mmol) and other reagents as described in Example 75(a) were used to afford 2.3 g of the required product. 1H NMR (DMSO-d6): 1.15 (3H, t), 4.15 (2H, q), 5.3 (4H, s), 7.0 (1H, s), 7.18 (2H, s), 7.64 (4H, d), 7.86 (4H, d).

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,5-dihydroxy benzoic acid ethyl ester 1.2 g (6.58 mmol), dissolved in 10 ml DMF, was added K2CO3 3.63 g (26.32 mmol) followed by 4-bromomethyl-benzonitrile 5.16 g (26.32 mmol) in 5 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and then heated to 35° C. for 8 h. The solvent was removed under reduced pressure and the residue was dissolved in 200 ml of ethyl acetate. The organic layer was washed with brine and water. Organic phase was dried over anhydrous sodium sulphate and solvent was removed under reduced pressure. The crude product was subjected to column chromatography and eluted using hexane:ethyl acetate (8:2) to afford 2.1 g of purified product. 1H NMR (DMSO-d6): 1.3 (3H, t), 4.3 (2H, q), 5.3 (4H, s), 7.0 (1H, s), 7.18 (2H, s), 7.64 (4H, d), 7.86 (4H, d). to attain RT The solvent was removed under reduced pressure the residue was dissolved in 200 ml of ethyl acetate The organic layer was washed with brine and water Organic phase was dried over anhydrous sodium sulphate and solvent was removed under reduced pressure eluted

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

Procedure: Potassium carbonate 6.7 g (48.5 mmol) followed by 4-fluoro benzonitrile 3.3 g (27.2 mmol) in 10 ml of DMF was added to a solution of 3,5-dihydroxy benzoic acid ethyl ester 5 g (27.4 mmol) in 20 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and was then heated to 45° C. for 10 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated. The crude compound was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 1.15 g of the required product. 1H NMR (DMSO-d6): δ 1.3 (3H, t), 4.3 (2H, q), 6.76 (1H, s), 7.02 (1H, s), 7.36 (2H, d), 7.24 (1H, s), 7.88 (2H, d), 10.3 (1H, s). to attain RT The reaction mixture was quenched with ice cold water extracted with ethyl acetate The organic layer was washed with water dried over anhydrous sodium sulphate concentrated The crude compound was purified by column chromatography

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

Procedure: Potassium carbonate 0.611 g (4.4 mmol) was added to a stirred solution of 3,5-dihydroxy-benzoic acid ethyl ester 0.5 g (1.7 mmol) dissolved in 15 ml of DMF and stirred for 10 min. This was followed by dropwise addition of 4-fluorobenzonitrile 0.82 g (6.8 mmol), dissolved in 5 ml of DMF, and the contents of the flask were stirred at 80° C. for 4 h. The reaction mixture was poured into ice-cold water, and extracted with ethyl acetate. The organic phase was washed with Na2CO3 and saturated brine solution, dried over sodium sulphate and concentrated to afford an oily residue which was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 0.4 g of the required product. The yield was 0.6 g. 1H NMR (DMSO-d6): δ 1.30 (3H, t), 4.30 (2H, q), 7.25 (2H, d), 7.32 (1H, t), 7.46 (2H, d), 7.90 (2H, d). the contents of the flask were stirred at 80° C. for 4 h The reaction mixture was poured into ice-cold water extracted with ethyl acetate The organic phase was washed with Na2CO3 and saturated brine solution dried over sodium sulphate concentrated to afford an oily residue which was purified by column chromatography

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate 2.1 g (15.2 mmol) dissolved in DMF solution was added to 3,5-dihydroxy-benzoic acid ethyl ester 1.5 g (8.2 mmol) dissolved in 15 ml of DMF. This was followed by dropwise addition of 6-chloro-nicotinonitrile 2.1 g (15.2 mmol) dissolved in 5 ml of DMF. After complete addition, the reaction mixture was stirred at 60° C. for 8-10 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated to afford a crude solid which was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 2.5 g of the required product. 1H NMR (DMSO-d6): δ 1.30 (3H, t), 4.32 (2H, q), 7.35 (2H, d), 7.52 (1H, t), 7.68 (2H, d), 8.39 (2H, d), 8.69 (2H, s). After complete addition The reaction mixture was quenched with ice cold water extracted with ethyl acetate The organic layer was washed with water dried over anhydrous sodium sulphate concentrated to afford a crude solid which was purified by column chromatography

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

Procedure: 308 g. of α-resorcylic acid were dissolved in 1000 ml of absolute ethanol and 25 ml of concentrated sulphuric acid were added. The reaction mixture was boiled under reflux for 20 hours. The ethanol was evaporated and the residue poured into water and extracted with ether. The etheral phase was washed with sodium bicarbonate solution and water and dried with magnesium sulphate. When the ether was evaporated, a crystallizing residue was obtained. under reflux for 20 hours The ethanol was evaporated the residue poured into water extracted with ether The etheral phase was washed with sodium bicarbonate solution and water dried with magnesium sulphate When the ether was evaporated a crystallizing residue was obtained

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

Procedure: 50 m mol of 3,5-dihydroxybenzoic acid ethyl ester, 120 m mol of stearyl bromide, and 110 m mol of sodium were made to react in ethanol, thereby forming 35 m mol of 3,5-dioctadecyloxybenzoic acid ethyl ester. This ester, 25 m mol, was first hydrolyzed into the corresponding acid, which in turn was converted into its acid chloride. The acid chloride was reacted in the same way as in Example 1, whereby 10 m mol of N-(3,5-dioctadecyloxybenzoyl)-N'methylsulfonyl-p-quinonediimine was obtained which is represented by the following formula: ##STR30##