4-dodecylbenzene-1,3-diol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-dodecylresorcinol (8.5 g, 30.53 mmole) (Aldrich Chemical Company) and 4-nitrosoresorcinol (5.0 g, 35.9 mmole) (Aldrich) in concentrated sulfuric acid (100 mL) is heated to 67° C. with stirring for 5 hours. The reaction mixture is allowed to cool to room temperature, poured into ice-water (1800 mL) and filtered. The resulting precipitate is washed with water until the filtrate is neutral to pH paper. This precipitate is dissolved in chloroform and the combined aqueous filtrates are back-extracted with chloroform (6×250 mL) to recover additional product. The combined chloroform layers are dried over anhydrous sodium sulfate and evaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c. (45:5:1 chloroform:methanol:triethylamine) Rf =0.69. An additional 5.58 g of product is obtained by neutralization of the aqueous filtrates above with 8M KOH and extraction with chloroform (total yield=8.13 g, 68%). 1H NMR (d6 -DMSO) δ:7.57(d,1H); 7.27(s,1H); 6.79(D,1H); 6.66(s,1H); 6.23(s,1H); 4.14(c,1H); 2.46(t,2H); 1.52(c,2H); 1.23(c,18H); 0.85(c,3H). filtered The resulting precipitate is washed with water until the filtrate This precipitate is dissolved in chloroform the combined aqueous filtrates are back-extracted with chloroform (6×250 mL) to recover additional product The combined chloroform layers are dried over anhydrous sodium sulfate evaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-dodecylresorcinol (8.5 g, 30.53 mmole) (Aldrich Chemical Company) and 4-nitrosoresorcinol (5.0 g, 35.9 mmole) (Aldrich) in concentrated sulfuric acid (100 mL) is heated to 67° C. with stirring for 5 hours. The reaction mixture is allowed to cool to room temperature, poured into ice-water (1800 mL) and filtered. The resulting precipitate is washed with water until the filtrate is neutral to pH paper. This precipitate is dissolved in chloroform and the combined aqueous filtrates are back-extracted with chloroform (6×250 mL) to recover additional product. The combined chloroform layers are dried over anhydrous sodium sulfate and evaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c. (45:5:1 chloroform:methanol:triethylamine) Rf =0.69. An additional 5.58 g of product is obtained by neutralization of the aqueous filtrates above with 8M KOH and extraction with chloroform (total yield=8.13 g, 68%). 1H NMR (d6 -DMSO) δ:7.57(d,1H); 7.27(s,1H); 6.79(D,1H); 6.66(s,1H); 6.23(s,1H); 4.14(c,1H); 2.46(t,2H); 1.52(c,2H); 1.23(c,18H); 0.85(c,3H). filtered The resulting precipitate is washed with water until the filtrate This precipitate is dissolved in chloroform the combined aqueous filtrates are back-extracted with chloroform (6×250 mL) to recover additional product The combined chloroform layers are dried over anhydrous sodium sulfate evaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 29.2 g of the product from (i) in 200 ml of acetic acid was added to 300 ml of 6 M hydrochloric acid to give a fine precipitate. To this was assed a zinc amalgam (made by intimately mixing 60 g of zinc, 6 g of mercury (II) chloride, 5 ml of conc. hydrochloric acid and 90 ml of water over 20 minutes. The mixture was heated at reflux for 5 hours; three further portions of 60 ml of conc. hydrochloric acid being added. After cooling, the filtered solids were taken up in chloroform, refiltered, and washed with 6 M hydrochloric acid, then water, dried and evaporated to give 26 g of the crude product. This was recrystallised from light petroleum (b.p. 60°-80° C.) to give 22.9 g of the product with a melting point of from 81°-82.5° C. to give a fine precipitate The mixture was heated at reflux for 5 hours After cooling washed with 6 M hydrochloric acid water, dried evaporated to give 26 g of the crude product This was recrystallised from light petroleum (b.p. 60°-80° C.)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-dodecylresorcinol (8.5 g, 30.53 mmole) (Aldrich Chemical Company) and 4-nitrosoresorcinol (5.0 g, 35.9 mmole) (Aldrich) in concentrated sulfuric acid (100 mL) is heated to 67° C. with stirring for 5 hours. The reaction mixture is allowed to cool to room temperature, poured into ice-water (1800 mL) and filtered. The resulting precipitate is washed with water until the filtrate is neutral to pH paper. This precipitate is dissolved in chloroform and the combined aqueous filtrates are back-extracted with chloroform (6×250 mL) to recover additional product. The combined chloroform layers are dried over anhydrous sodium sulfate and evaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c. (45:5:1 chloroform:methanol:triethylamine) Rf =0.69. An additional 5.58 g of product is obtained by neutralization of the aqueous filtrates above with 8M KOH and extraction with chloroform (total yield=8.13 g, 68%). 1H NMR (d6 -DMSO) δ:7.57(d,1H); 7.27(s,1H); 6.79(D,1H); 6.66(s,1H); 6.23(s,1H); 4.14(c,1H); 2.46(t,2H); 1.52(c,2H); 1.23(c,18H); 0.85(c,3H). filtered The resulting precipitate is washed with water until the filtrate This precipitate is dissolved in chloroform the combined aqueous filtrates are back-extracted with chloroform (6×250 mL) to recover additional product The combined chloroform layers are dried over anhydrous sodium sulfate evaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c