甲基4-羟基-3-(羟甲基)苯甲酸盐

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound obtained in (b) (182 mg, 1 mmol) was mixed successfully with 2 ml of acetonitrile and triphenylphosphine hydrobromide (361 mg, 1.05 mmol). After heating at reflux for one hour fifteen minutes, the reaction medium was cooled and evaporated to dryness, ethyl ether was added, the mixture was filtered and the precipitate was washed with ethyl ether. After drying in an oven, 470 mg of a white solid were obtained, equivalent to a yield of 93%. Its properties were as follows: After heating at reflux for one hour fifteen minutes the reaction medium was cooled evaporated to dryness, ethyl ether was added the mixture was filtered the precipitate was washed with ethyl ether After drying in an oven

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound obtained in (b) (182 mg, 1 mmol) was mixed successfully with 2 ml of acetonitrile and triphenylphosphine hydrobromide (361 mg, 1.05 mmol). After heating at reflux for one hour fifteen minutes, the reaction medium was cooled and evaporated to dryness, ethyl ether was added, the mixture was filtered and the precipitate was washed with ethyl ether. After drying in an oven, 470 mg of a white solid were obtained, equivalent to a yield of 93%. Its properties were as follows: After heating at reflux for one hour fifteen minutes the reaction medium was cooled evaporated to dryness, ethyl ether was added the mixture was filtered the precipitate was washed with ethyl ether After drying in an oven

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound obtained in (a) (1.80 g, 10 mmol) was mixed with 50 ml of methanol, and sodium borohydride (189 mg, 5 mmol) was added portionwise while maintaining the temperature below 20° C. After stirring for 5 minutes at room temperature, the methanol was evaporated off and the medium was then poured onto a 6N HCl/ice mixture, extracted with ethyl ether, washed with water to neutral pH, dried over magnesium sulfate and filtered, and the solvents were evaporated off. The properties of the final product were as follows: was added portionwise while maintaining the temperature below 20° C the methanol was evaporated off the medium was then poured onto a 6N HCl/ice mixture extracted with ethyl ether washed with water to neutral pH dried over magnesium sulfate filtered the solvents were evaporated off

反应条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To MeOH (100 mL) was added methyl 4-hydroxy-3-(hydroxymethyl)benzoate (10 g; 54.89 mmol; 1 eq.) and PTSA (1.89 g; 10.98 mmol; 0.20 eq.). The resulting suspension was heated to 130° C. for 1 hour. The reaction mixture was concentrated giving a yellow solid. It was dissolved in EtOAc (400 mL), washed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as an orange solid (9.59 g, 89%). 1H NMR (DMSO-d6, 300 MHz) δ 10.48 (br s, 1H), 7.87-7.86 (d, J=2.11 Hz, 1H), 7.76-7.28 (dd, J=8.44 Hz, 2.31 Hz, 1H), 6.91-6.88 (d, J=8.48 Hz, 1H), 4.39 (s, 2H), 3.79 (s, 3H), 3.33 (s, 3H). LC/MS (Method B): 195.2 (M−H)−. The reaction mixture was concentrated giving a yellow solid washed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL) dried over MgSO4 concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methyl 3-formyl-4-hydroxybenzoate (19.80 g; 109.90 mmol; 1 eq.) in MeOH (396 mL) was added at 0° C. NaBH4 (6.24 g; 164.85 mmol; 1.50 eq.) in several portions (portions over 20 min). The reaction mixture was stirred at RT for 2 hours. The reaction mixture was concentrated and the residue was suspended in EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NH4Cl (2×200 mL), water (200 mL), then brine (200 mL). The aqueous layer contained a lot of the desired compound so it was saturated with NaCl and extracted with EtOAc (4×600 mL). Organics were combined, dried over MgSO4 and concentrated affording the title compound as a beige solid (10.52 g, 52%). LC/MS (Method B): 181.1 (M−H)−. in several portions (portions over 20 min) The reaction mixture was concentrated The organic layer was washed with a saturated aqueous solution of NH4Cl (2×200 mL), water (200 mL) extracted with EtOAc (4×600 mL) dried over MgSO4 concentrated

反应条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To MeOH (100 mL) was added methyl 4-hydroxy-3-(hydroxymethyl)benzoate (10 g; 54.89 mmol; 1 eq.) and PTSA (1.89 g; 10.98 mmol; 0.20 eq.). The resulting suspension was heated to 130° C. for 1 hour. The reaction mixture was concentrated giving a yellow solid. It was dissolved in EtOAc (400 mL), washed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as an orange solid (9.59 g, 89%). 1H NMR (DMSO-d6, 300 MHz) δ 10.48 (br s, 1H), 7.87-7.86 (d, J=2.11 Hz, 1H), 7.76-7.28 (dd, J=8.44 Hz, 2.31 Hz, 1H), 6.91-6.88 (d, J=8.48 Hz, 1H), 4.39 (s, 2H), 3.79 (s, 3H), 3.33 (s, 3H). LC/MS (Method B): 195.2 (M−H)−. The reaction mixture was concentrated giving a yellow solid washed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL) dried over MgSO4 concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methyl 3-formyl-4-hydroxybenzoate (19.80 g; 109.90 mmol; 1 eq.) in MeOH (396 mL) was added at 0° C. NaBH4 (6.24 g; 164.85 mmol; 1.50 eq.) in several portions (portions over 20 min). The reaction mixture was stirred at RT for 2 hours. The reaction mixture was concentrated and the residue was suspended in EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NH4Cl (2×200 mL), water (200 mL), then brine (200 mL). The aqueous layer contained a lot of the desired compound so it was saturated with NaCl and extracted with EtOAc (4×600 mL). Organics were combined, dried over MgSO4 and concentrated affording the title compound as a beige solid (10.52 g, 52%). LC/MS (Method B): 181.1 (M−H)−. in several portions (portions over 20 min) The reaction mixture was concentrated The organic layer was washed with a saturated aqueous solution of NH4Cl (2×200 mL), water (200 mL) extracted with EtOAc (4×600 mL) dried over MgSO4 concentrated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound obtained in (b) (182 mg, 1 mmol) was mixed successfully with 2 ml of acetonitrile and triphenylphosphine hydrobromide (361 mg, 1.05 mmol). After heating at reflux for one hour fifteen minutes, the reaction medium was cooled and evaporated to dryness, ethyl ether was added, the mixture was filtered and the precipitate was washed with ethyl ether. After drying in an oven, 470 mg of a white solid were obtained, equivalent to a yield of 93%. Its properties were as follows: After heating at reflux for one hour fifteen minutes the reaction medium was cooled evaporated to dryness, ethyl ether was added the mixture was filtered the precipitate was washed with ethyl ether After drying in an oven

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound obtained in (a) (1.80 g, 10 mmol) was mixed with 50 ml of methanol, and sodium borohydride (189 mg, 5 mmol) was added portionwise while maintaining the temperature below 20° C. After stirring for 5 minutes at room temperature, the methanol was evaporated off and the medium was then poured onto a 6N HCl/ice mixture, extracted with ethyl ether, washed with water to neutral pH, dried over magnesium sulfate and filtered, and the solvents were evaporated off. The properties of the final product were as follows: was added portionwise while maintaining the temperature below 20° C the methanol was evaporated off the medium was then poured onto a 6N HCl/ice mixture extracted with ethyl ether washed with water to neutral pH dried over magnesium sulfate filtered the solvents were evaporated off

反应条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To MeOH (100 mL) was added methyl 4-hydroxy-3-(hydroxymethyl)benzoate (10 g; 54.89 mmol; 1 eq.) and PTSA (1.89 g; 10.98 mmol; 0.20 eq.). The resulting suspension was heated to 130° C. for 1 hour. The reaction mixture was concentrated giving a yellow solid. It was dissolved in EtOAc (400 mL), washed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as an orange solid (9.59 g, 89%). 1H NMR (DMSO-d6, 300 MHz) δ 10.48 (br s, 1H), 7.87-7.86 (d, J=2.11 Hz, 1H), 7.76-7.28 (dd, J=8.44 Hz, 2.31 Hz, 1H), 6.91-6.88 (d, J=8.48 Hz, 1H), 4.39 (s, 2H), 3.79 (s, 3H), 3.33 (s, 3H). LC/MS (Method B): 195.2 (M−H)−. The reaction mixture was concentrated giving a yellow solid washed with a saturated aqueous solution of NaHCO3 (200 mL), brine (200 mL) dried over MgSO4 concentrated