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Preparation method and intermediate of 2-phenethylphenol derivative and intermediate
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A technology of phenethylphenol and its derivatives, which is applied in the field of preparation of 2-phenethylphenol derivatives and their intermediates and intermediates, can solve the problems of cumbersome steps, many by-products, harsh operating conditions, etc. Simple handling, high overall yield, and easy purification
Active Publication Date: 2019-08-09
LIANHE CHEM TECH TAIZHOU
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[0019] The technical problem to be solved by the present invention is to overcome the high cost, cumbersome steps, harsh operating conditions, high requirements for equipment, potential safety hazards, many by-products and separation of 2-phenylethylphenol derivatives in the prior art. Difficult, complex post-processing, low yield, polluting the environment, unfavorable for industrialized production and other defects, but provide the preparation method and intermediates of 2-phenylethylphenol derivatives and their intermediates
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Embodiment 1
[0086]
[0087]Put 59g of 60% sodiumhydrogen (1.47mol) in 140mL / 140mL THF / toluene mixture, cool and stir in an ice-water bath, add 94g (0.7mol) of benzofuranone and 119g (0.7mol) of m-methoxyl dropwise at 10-20°C Add 70mL / 50mL THF / toluene solution of benzoyl chloride, stir at 10-20°C for 6 hours after addition, add 1200mL toluene and distill under reduced pressure to recover THF. Add 450mL 3M hydrochloric acid and 200mL water dropwise, separate the organic phase, wash it twice with water, once with saturated sodiumchloride, concentrate the organic phase, add methanol for recrystallization, and obtain 153g of 3-(hydroxy(3-methoxyphenyl)methylene ) Benzofuran-2(3H)-one. Yield 81%, HPLC purity 99%.
[0091] Put 59g of 60% sodiumhydrogen (1.47mol) in 140mL / 140mL THF / toluene mixture, cool and stir in an ice-water bath, add 94g (0.7mol) of benzofuranone and 98g (0.7mol) of benzoyl chloride dropwise at 10-20°C 70mL / 50mL THF / toluene solution, stir at 10-20°C for 6 hours after addition, add 1200mL toluene and distill under reduced pressure to recover THF. Add 450mL 3M hydrochloric acid and 200mL water dropwise, separate the organic phase, wash it twice with water, once with saturated sodium chloride, concentrate the organic phase, add methanol for recrystallization, and obtain 150g of 3-(hydroxy(phenyl)methylene)benzofuran- 2(3H)-one. Yield 90%, HPLC purity 99%.
[0095] 59g of 60% sodium hydrogen (1.47mol) was placed in 140mL / 140mL THF / toluene mixture, cooled and stirred in an ice-water bath, 94g (0.7mol) of benzofuranone and 122.5g (0.7mol) of 3-chloro Add 70mL / 50mL THF / toluene solution of benzoyl chloride, stir at 10-20°C for 6 hours after addition, add 1200mL toluene and distill under reduced pressure to recover THF. Add dropwise 450mL of 3M hydrochloric acid and 200mL of water, separate the organic phase, wash it twice with water, once with saturated sodium chloride, concentrate the organic phase, add methanol for recrystallization, and obtain 156g of 3-(hydroxy(3-chlorophenyl)methylene)benzene And furan-2(3H)-one. Yield 82%, HPLC purity 99%.
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Abstract
The invention discloses a preparation method of a 2-phenethyl phenol derivative. The preparation method of the 2-phenethyl phenol derivative comprises following steps: a compound represented in a formula 5 is subjected to a reduction reaction, a compound represented in a formula 1 is prepared, wherein the compound represented in the formula 5 is prepared from a compound represented in a formula 4 through an ester hydrolysis reaction and a decarboxylic reaction, the compound represented in the formula 4 is prepared from a compound represented in a formula 2 and a compound represented in a formula 3 through a condensation reaction, and R is hydrogen, halogen, C1-C3 alkyl or C1-C3 alkoxy. The preparation methods of the 2-phenethyl phenol derivative and an intermediate of the 2-phenethyl phenol derivative are low in cost and safe to operate, the steps and the after-treatment are simple, a few by-products are produced, the intermediate product and the final product are both easy to purify, the total yield and the purity are higher, and industrial production is facilitated.
Description
technical field [0001] The invention specifically relates to a preparation method and intermediates of 2-phenethylphenol derivatives and intermediates thereof. Background technique [0002] Sagrelate is a 5-hydroxytryptamine (5-HT2) receptorselective antagonist with high-efficiency biological activity. It inhibits platelet aggregation by selectively antagonizing the combination of 5-HT2 and HT2 receptors, especially Inhibition of platelet aggregation and vasoconstriction enhanced by serotonin can be used to improve ischemic symptoms such as ulcers, pain and cold sensation caused by chronic arterial occlusive disease. For details, refer to patent JP98102910. [0003] 2-Phenylethylphenol derivatives are the key intermediates for the preparation of sagrelate, and they have certain biological activities. For example, the compounds R-102444 and R-96544 developed by Daiichi Sankyo have entered the stage of clinical research for antiplatelet therapy and the treatment of periphera...
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