A kind of method for preparing 2', 4'-dihydroxyacetophenone-2'-carboxylate
A technology of dihydroxyacetophenone and carboxylic acid ester, which is applied in the preparation of carboxylic acid halides, the preparation of ester groups and hydroxyl groups, organic chemistry, etc., and can solve the problems of poor atom economy, difficulty in structural transformation of natural products, and difficult acetylation, etc. problems, to achieve the effect of simple operation, high yield and high atom economy
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Embodiment 1
[0025] The preparation of embodiment 1 compound I
[0026] (1) 1.52 g of 2',4'-dihydroxyacetophenone was dissolved in 5 mL of pyridine, and 20 mL of dichloromethane was added. Stir and cool to 0°C in an ice-water bath, slowly add 0.71 mL of acetyl chloride dropwise, slowly rise to room temperature and monitor the reaction with TLC. After the reaction is complete, pour the reaction solution into 50 mL 1N HCl, extract three times with 20 mL ethyl acetate, wash three times with 20 mL 1N HCl, once with 60 mL of distilled water, and twice with 60 mL of saturated saline, dry over night with anhydrous sodium sulfate, and extract Filtration, and the filtrate was spin-dried to obtain 1.93 g of 2',4'-dihydroxyacetophenone-4'-acetate.
[0027] (2) Dissolve 194 mg of 2', 4'-dihydroxyacetophenone-4'-acetate in 2 mL of DMSO, add 138 mg of K 2 CO 3 , the reaction was stirred at 25°C and monitored by TLC. After the reaction is complete, pour the reaction solution into 20mL 1N HCl, extract...
Embodiment 2
[0029] The preparation of embodiment 2 compound II
[0030] (1) 1.52 g of 2',4'-dihydroxyacetophenone was dissolved in 5 mL of pyridine, and 20 mL of dichloromethane was added. Stir and cool to 0°C in an ice-water bath, slowly add 0.87mL propionyl chloride dropwise, slowly rise to room temperature and monitor the reaction with TLC. After the reaction is complete, pour the reaction solution into 50 mL 1N HCl, extract three times with 20 mL ethyl acetate, wash three times with 20 mL 1N HCl, once with 60 mL of distilled water, and twice with 60 mL of saturated saline, dry over night with anhydrous sodium sulfate, and extract Filtration, and the filtrate was spin-dried to obtain 1.72 g of 2',4'-dihydroxyacetophenone-4'-propionate.
[0031] (2) Dissolve 208 mg of 2', 4'-dihydroxyacetophenone-4'-propionate in 2 mL of DMSO, add 138 mg of K 2 CO 3 , the reaction was stirred at 25°C and monitored by TLC. After the reaction is complete, pour the reaction solution into 20mL 1N HCl, e...
Embodiment 3
[0033] The preparation of embodiment 3 compound III
[0034] (1) 1.52 g of 2',4'-dihydroxyacetophenone was dissolved in 5 mL of pyridine, and 20 mL of dichloromethane was added. Stir and cool to 0°C in an ice-water bath, slowly add 1.15 mL of benzoyl chloride dropwise, slowly rise to room temperature and monitor the reaction with TLC. After the reaction is complete, pour the reaction solution into 50 mL 1N HCl, extract three times with 20 mL ethyl acetate, wash three times with 20 mL 1N HCl, once with 60 mL of distilled water, and twice with 60 mL of saturated saline, dry over night with anhydrous sodium sulfate, and extract Filtration, and the filtrate was spin-dried to obtain 2.23 g of 2',4'-dihydroxyacetophenone-4'-benzoate.
[0035] (2) Dissolve 256mg of 2′,4′-dihydroxyacetophenone-4′-benzoate in 2mL of DMSO, add 138mg of K 2 CO 3 , the reaction was stirred at 25°C and monitored by TLC. After the reaction is complete, pour the reaction solution into 20mL 1N HCl, extract ...
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