4-(甲氧基甲氧基)苯甲醛

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

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: 4-hydroxybenzaldehyde (1.22 g, 10 mmol) was dissolved in 100 ml dried DMF and stirred at room temperature. NaH (0.8 g) was added in to the reaction. After 10 min, MOMCl (1.5 ml) was added into the reaction by drop. Then the result solution was stirred at room temperature, and monitored by TLC. When the reaction was completed, 500 ml H2O was added. The resulting solution was extracted by ethyl acetate, and the organic layers were combined, dried by Na2SO4, concentrated by reduce pressure. The resulting oil was directly used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ: 3.50 (s, 3H), 5.26 (s, 2H), 7.14 (d, J=8.8 Hz, 2H), 7.83 (d, J=8.8 Hz, 2H), 9.90 (s, 1H). Then the result solution was stirred at room temperature The resulting solution was extracted by ethyl acetate dried by Na2SO4 concentrated The resulting oil was directly used in the next step without further purification

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

实验步骤: In 50 ml of ethanol were dissolved 6.31 g of the 2',4'-bis(methoxymethoxy)acetophenone obtained in Production Example 10 and 4.00 g of the p-methoxymethoxybenzaldehyde obtained in Production Example 25, and the solution was cooled to 0° C. and 30 ml of a saturated solution of potassium hydroxide in ethanol was added to the solution. The temperature of the reaction liquid was elevated to room temperature and the liquid was stirred for 2 days. The reaction liquid was diluted with water, neutralized with 6N hydrochloric acid and extracted with ethyl acetate, and the organic layer was dried with sodium sulfate and concentrated under reduced pressure to obtain a reaction mixture in the form of a syrup. The syrup was subjected to the column chromatography (320 g of 270-400 mesh Kieselgel 60; 0.5 kg/cm2 ; eluting solvent: hexane/ethyl acetate=1). Fractions of 50 ml were collected and the 66th to 87th fractions were combined to obtain 5.64 g (yield=55.9 %) of 2',4,4'-tris(methoxymethoxy)chalcone.

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

实验步骤: In 3 ml of methanol were dissolved 1.40 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-isopentylacetophenone obtained in Production Example 16 and 715 mg of the p-methoxymethoxybenzaldehyde obtained in Production Example 25, and a 50% ethanol solution of sodium hydroxide (4.0 g/8 ml) was added to the solution and the mixture was stirred at room temperature for 1 day to effect a reaction.

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

实验步骤: In 30 ml of methanol were dissolved 14.73 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl-2-butenyl)acetophenone obtained in Production Example 13 and 7.55 g of the p-methoxymethoxybenzaldehyde obtained in Production Example 25, and a saturated solution of sodium hydroxide in methanol was added to the solution and the mixture was stirred at room temperature for 1 day to effect a reaction. After the reaction, the reaction mixture was carefully neutralized with dilute hydrochloric acid and extracted with 1.5 l of ethyl acetate, and the ethyl acetate layer was washed with water (500 ml×4 times), shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation to obtain 18.94 g (yield=88.2%) of 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone in the form of a yellow oil.

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

实验步骤: In 40 ml of ethanol were dissolved 20.4 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone obtained in Production Example 6 and 13.7 g of the p-methoxymethoxybenzaldehyde obtained in Production Example 23, and a 50% solution of potassium hydroxide in ethanol was added to the solution and the mixture was stirred at room temperature overnight to effect a reaction. After the reaction, the reaction mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate, and the solvent was removed from the ethyl acetate layer by distillation. The obtained residue was crystallized from methanol to obtain 26.3 g (yield=85.9%) of 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-(2-propenyl)chalcone in the form of a yellow prism.

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

实验步骤: In 40 ml of ethanol were dissolved 20.4 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone obtained in Production Example 6 and 13.7 g of the p-methoxymethoxybenzaldehyde obtained in Production Example 23, and a 50% solution of potassium hydroxide in ethanol was added to the solution and the mixture was stirred at room temperature overnight to effect a reaction. After the reaction, the reaction mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate, and the solvent was removed from the ethyl acetate layer by distillation. The obtained residue was crystallized from methanol to obtain 26.3 g (yield=85.9%) of 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-(2-propenyl)chalcone in the form of a yellow prism.

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

实验步骤: To a mixture of carbon tetrabromide (56.58 g), triphenylphosphine (44.61 g) and zinc powder (11.18 g) was added dichloromethane (300 ml), and the mixture was stirred for 25 hours at room temperature. To the mixture was then added p-methoxymethoxybenzaldehyde (13.91 g), which was stirred for 30 hours. The reaction mixture was subjected to filtration through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 4-(2,2-dibromoethenyl)phenol methoxymethyl ether (17.84 g) (Compound B-25). The physical properties are shown in Table 7. The reaction mixture was subjected to filtration through celite the filtrate was concentrated under reduced pressure The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

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

实验步骤: To a mixture of carbon tetrabromide (56.58 g), triphenylphosphine (44.61 g) and zinc powder (11.18 g) was added dichloromethane (300 ml), and the mixture was stirred for 25 hours at room temperature. To the mixture was then added p-methoxymethoxybenzaldehyde (13.91 g), which was stirred for 30 hours. The reaction mixture was subjected to filtration through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 4-(2,2-dibromoethenyl)phenol methoxymethyl ether (17.84 g) (Compound B-25). The physical properties are shown in Table 7. The reaction mixture was subjected to filtration through celite the filtrate was concentrated under reduced pressure The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

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

实验步骤: 2-[(4-methoxymethoxybenzylidene)amino]-3-methylphenol (F6) was prepared in a similar manner for the preparation of 2-[(5-Methoxy-2-methoxymethoxybenzylidene)amino]-3-methylphenol (F4) by using 4-methoxymethoxybenzaldehyde (F3) (3.32 g, 20 mmol) instead of 5-methoxy-2-methoxymethoxybenzaldehyde (F1) in 84% (4.56 g): 1H-NMR (500 MHz, CDCl3) δ3.53 (s, 3H), 5.24 (s, 3H), 7.17 (d, 1H, J=9.0 Hz), 7.35 (d, 1H, J=9.0 Hz), 10.52 (s, 1H).