1,16-Dibromohexadecane

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

実験手順: Starting from 4-ethyl-2-aminopyridine described by Hansch and 1,16-dibromohexadecane, the derivative of the title, m.p. 105°/110° C., is obtained. the derivative of the title, m.p. 105°/110° C., is obtained

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

実験手順: An acetone solution of 90 m moles(21.8 g) of 4'-hydroxybiphenyl-4-carboxylic acid ethyl ester obtained in Example 24, 0.15 mole(57.6 g) of 1,16-dibromohexadecane, and 0.4 mole(55.3 g) of potassium carbonate was refluxed for four hours. The reaction solution was filtered. The filtrate was concentrated, and then purified by column chromatography to obtain 34.4 g of 4'-(16-bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 70%) The reaction solution was filtered The filtrate was concentrated purified by column chromatography

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

実験手順: The diol 14 (1.047 g, 4.05 mmol) was dissolved in cyclohexane (30 mL) and vigorously stirred with 48% HBr (0.5 mL, 4.46 mmol, 1.1 eq.). The mixture was refluxed for 6 h, diluted with water (50 mL) and the phases were separated. The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3×20 mL). The combined organic layer was dried over MgSO4. The product was purified by column chromatography with silica gel (6×6 cm, cyclohexane/ethyl acetate, 8:1) and isolated as a white solid. Yield: 4.598 g (96%). Traces of 1,16-dibromohexadecane were also found. The mixture was refluxed for 6 h the phases were separated The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3×20 mL) The combined organic layer was dried over MgSO4 The product was purified by column chromatography with silica gel (6×6 cm, cyclohexane/ethyl acetate, 8:1) isolated as a white solid

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

実験手順: Starting from 4-ethyl-2-aminopyridine described by Hansch and 1,16-dibromohexadecane, the derivative of the title, m.p. 105°/110° C., is obtained. the derivative of the title, m.p. 105°/110° C., is obtained

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

実験手順: An acetone solution of 90 m moles(21.8 g) of 4'-hydroxybiphenyl-4-carboxylic acid ethyl ester obtained in Example 24, 0.15 mole(57.6 g) of 1,16-dibromohexadecane, and 0.4 mole(55.3 g) of potassium carbonate was refluxed for four hours. The reaction solution was filtered. The filtrate was concentrated, and then purified by column chromatography to obtain 34.4 g of 4'-(16-bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 70%) The reaction solution was filtered The filtrate was concentrated purified by column chromatography

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

実験手順: An acetone solution of 90 m moles (21.8 g) of 4'-hydroxybiphenyl-4-carboxylic acid ethyl ester obtained in Example 24, 0.15 mole (57.6 g) of 1,16-dibromohexadecane, and 0.4 mole (55.3 g) of potassium carbonate was refluxed for four hours. The reaction solution was filtered. The filtrate was concentrated, and then purified by column chromatography to obtain 34.4 g of 4'-(16-bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 70%) The reaction solution was filtered The filtrate was concentrated purified by column chromatography

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

実験手順: The crystalline form of the derivative defined in the title is obtained using the -1,16-dibromohexadecane derivative and tripropylamine according to the conditions described above, M.P. 227° C. is obtained

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

実験手順: The diol 14 (1.047 g, 4.05 mmol) was dissolved in cyclohexane (30 mL) and vigorously stirred with 48% HBr (0.5 mL, 4.46 mmol, 1.1 eq.). The mixture was refluxed for 6 h, diluted with water (50 mL) and the phases were separated. The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3×20 mL). The combined organic layer was dried over MgSO4. The product was purified by column chromatography with silica gel (6×6 cm, cyclohexane/ethyl acetate, 8:1) and isolated as a white solid. Yield: 4.598 g (96%). Traces of 1,16-dibromohexadecane were also found. The mixture was refluxed for 6 h the phases were separated The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3×20 mL) The combined organic layer was dried over MgSO4 The product was purified by column chromatography with silica gel (6×6 cm, cyclohexane/ethyl acetate, 8:1) isolated as a white solid

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

実験手順: Starting from 4-ethyl-2-aminopyridine described by Hansch and 1,16-dibromohexadecane, the derivative of the title, m.p. 105°/110° C., is obtained. the derivative of the title, m.p. 105°/110° C., is obtained

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

実験手順: An acetone solution of 90 m moles(21.8 g) of 4'-hydroxybiphenyl-4-carboxylic acid ethyl ester obtained in Example 24, 0.15 mole(57.6 g) of 1,16-dibromohexadecane, and 0.4 mole(55.3 g) of potassium carbonate was refluxed for four hours. The reaction solution was filtered. The filtrate was concentrated, and then purified by column chromatography to obtain 34.4 g of 4'-(16-bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 70%) The reaction solution was filtered The filtrate was concentrated purified by column chromatography