反式-3-羟基肉桂酸甲酯

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

实验步骤: To a solution of (E)-methyl 3-(3-hydroxyphenyl)acrylate (15.8 g) in methanol (150 mL) was added 10% palladium-activated carbon (1.50 g) and, under a hydrogen atmosphere, the mixture was stirred at room temperature for 5 hr. The reaction mixture was filtered to remove palladium carbon, and the filtrate was evaporated under reduced pressure to give the title compound (16.0 g) as a colorless oil. This compound was used for the next step without further purification. The reaction mixture was filtered to remove palladium carbon the filtrate was evaporated under reduced pressure

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (E)-3-(3-hydroxyphenyl)acrylic acid (15.0 g) in methanol (100 mL) was added sulfuric acid (2.0 mL), and the mixture was stirred at 70° C. for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.8 g) as white crystals. This compound was used for the next step without further purification. the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (E)-3-(3-hydroxyphenyl)acrylic acid (15.0 g) in methanol (100 mL) was added sulfuric acid (2.0 mL), and the mixture was stirred at 70° C. for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.8 g) as white crystals. This compound was used for the next step without further purification. the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure

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

实验步骤: 10% Palladium on carbon (0.31 g) was added to a solution of trans-3-(3-hydroxyphenyl)acrylic acid methyl ester (31.0 g, 17.4 mmol) (prepared as described in Example 6A) in ethyl acetate (30 mL) at room temperature under a nitrogen atmosphere. The mixture was hydrogenated under a balloon pressure for 4 hours. The catalyst was filtered, and the filtrate was concentrated to dryness. Crude 3-(3-hydroxyphenyl)propionic acid methyl ester (3.16 g) was directly used in the next step. The catalyst was filtered the filtrate was concentrated to dryness

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

实验步骤: A solution of trimethyl phosphonoacetate (9.94 mL, 61.4 mmol), lithium chloride (2.60 g, 12.2 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (15.92 mL, 106.5 mmol) in acetonitrile (80 mL) at room temperature under a nitrogen atmosphere was stirred at room temperature for 30 minutes. 3-Hydroxybenzaldehyde (5.00 g, 40.9 mmol) was added, and the mixture was stirred at room temperature for an additional 3 hours. Water was added and the aqueous phase was extracted with diethyl ether. The combined organic fractions were washed with water, brine, dried over magnesium sulfate, and evaporated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave trans-3-(3-hydroxyphenyl)acrylic acid methyl ester as a white crystalline solid (6.30 g, 86%). the aqueous phase was extracted with diethyl ether The combined organic fractions were washed with water, brine dried over magnesium sulfate evaporated to dryness Purification by flash chromatography eluting with hexane/ethyl acetate

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

实验步骤: To a solution of (E)-methyl 3-(3-hydroxyphenyl)acrylate (15.8 g) in methanol (150 mL) was added 10% palladium-activated carbon (1.50 g) and, under a hydrogen atmosphere, the mixture was stirred at room temperature for 5 hr. The reaction mixture was filtered to remove palladium carbon, and the filtrate was evaporated under reduced pressure to give the title compound (16.0 g) as a colorless oil. This compound was used for the next step without further purification. The reaction mixture was filtered to remove palladium carbon the filtrate was evaporated under reduced pressure

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (E)-3-(3-hydroxyphenyl)acrylic acid (15.0 g) in methanol (100 mL) was added sulfuric acid (2.0 mL), and the mixture was stirred at 70° C. for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.8 g) as white crystals. This compound was used for the next step without further purification. the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure