Process for producing cinnamaldehyde derivatives, use thereof and the like
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-045/72
C07C-045/73
출원번호
US-0295997
(2002-11-18)
우선권정보
JP-0142811 (2000-05-16)
발명자
/ 주소
Mori, Kenichi
Fujita, Shinji
Funakoshi, Nao
Takemoto, Tadashi
출원인 / 주소
Ajinomoto Co., Ltd.
대리인 / 주소
Oblon, Spivak, McClelland, Maier &
인용정보
피인용 횟수 :
2인용 특허 :
1
초록▼
A process for conveniently and efficiently producing a highly pure cinnamaldehyde derivative, for example, (2E)-(3-hydroxy-4-methoxy)cinnamaldehyde, which comprises reacting a benzaldehyde derivative, such as isovanillin and the like, with acetaldehyde in the presence of an alkali, in particular pre
A process for conveniently and efficiently producing a highly pure cinnamaldehyde derivative, for example, (2E)-(3-hydroxy-4-methoxy)cinnamaldehyde, which comprises reacting a benzaldehyde derivative, such as isovanillin and the like, with acetaldehyde in the presence of an alkali, in particular preferably, dropping acetaldehyde little by little thereto in an aqueous solution at a low temperature for the reaction thereof. The cinnamaldehyde derivative thus obtained is selectively reduced to produce 3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propionaldehyde. Further, through a reductive alkylation reaction of the compound thus produced with an aspartame, N-[N-[3-(3-hydroxy-4-substituted (with methoxy group or the like)phenyl) propyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester, which is useful as a sweetener having a high sweetening potency, can be industrially and efficiently produced. The processes therefor are also provided.
대표청구항▼
1. A process for producing a cinnamaldehyde compound represented by formula (II) or a salt thereof: comprising:reacting a benzaldehyde compound represented by formula (I): with acetaldehyde in the presence of an alkali, wherein R is a methoxy group. 2. The process as defined in claim 1, wherein said
1. A process for producing a cinnamaldehyde compound represented by formula (II) or a salt thereof: comprising:reacting a benzaldehyde compound represented by formula (I): with acetaldehyde in the presence of an alkali, wherein R is a methoxy group. 2. The process as defined in claim 1, wherein said reacting is conducted in an aqueous solution at a temperature in the range of 0 to ?20° C.3. The process as defined in claim 1, wherein said acetaldehyde is added to said benzaldehyde compound in an aqueous solution over a period of 12 to 96 hours.4. The process as defined in claim 2, wherein said acetaldehyde is added to said benzaldehyde compound in an aqueous solution at a temperature in the range of 0 to ?20° C. over a period of 12 to 96 hours.5. The process as defined in claim 1, wherein said acetaldehyde is added to said benzaldehyde compound in an aqueous solution at a temperature in the range of 0 to ?20° C. over a period of 12 to 96 hours.6. The process as defined in claim 1, wherein said alkali is a metal hydroxide or an amine.7. A process for producing a propionaldehyde compound represented by formula (III): comprising: producing a cinnamaldehyde compound represented by formula (II) according to the process of claim 1, and subjecting said cinnamaldehyde compound represented by formula (II) to a reaction for reducing a carbon-carbon double bond selectively with hydrogen in the presence of a reduction catalyst, wherein R is a methoxy group. 8. The process as defined in claim 7, wherein said reaction for reducing a carbon-carbon double bond selectively is a hydrogenation reaction in the presence of a catalyst for hydrogenation.9. The process as defined in claim 7, wherein said reduction catalyst is a palladium-, platinum-, or rhodium-based catalyst.10. A crystal of (2E)-(3-hydroxy-4-methoxy)cinnamaldehyde having a purity of at least 95% by weight.11. The crystal as defined in claim 10, which shows X-ray diffraction peaks at diffraction angles of at least 13.75°, 16.53°, 24.43° and 27.75° (2θ, CuKαray) when examined by powder X-ray diffractometry.12. The crystal as defined in claim 10, which has melting point of 149 to 152° C.13. The process as defined in claim 1, wherein said alkali is selected from the group consisting of sodium hydroxide, potassium hydroxide, and mixtures thereof.14. The process as defined in claim 1, wherein said alkali is diethylamine.15. The process as defined in claim 1, wherein said alkali is present in an amount of 5 to 15 molar equivalents based on the moles of said benzaldehyde compound.16. The process as defined in claim 1, wherein said reacting is conducted in a solvent selected from the group consisting of water, methanol, and mixtures thereof.17. The process as defined in claim 1, wherein said benzaldehyde compound and said acetaldehyde are reacted in a ratio of 1.5 to 3 molar equivalents of said acetaldehyde based on the moles of said benzaldehyde compound.18. The process as defined in claim 7, wherein said reaction for reducing a carbon-carbon double bond selectively is conducted in a solvent selected from the group consisting of methanol, ethanol, tetrahydrofuran, acetonitrile, dimethylformamide, mixtures thereof, and mixtures thereof with water.19. The process as defined in claim 7, wherein said reaction for reducing a carbon-carbon double bond selectively is conducted in a solvent selected from the group consisting of methanol and mixtures of methanol and water.20. The process as defined in claim 8, wherein said hydrogenation reaction is conducted at a hydrogen pressure of 0.01 to 1.0 MPa.21. The process as defined in claim 8, wherein said hydrogenation reaction is conducted at a hydrogen pressure of 0.01 to 0.1 MPa.22. The process as defined in claim 8, wherein said hydrogenation reaction is conducted at a temperature of 25 to 50° C.23. The process as defined in claim 8, wherein said hydrogenation reaction is conducted at a temperature of 30 to 40° C.24. The process as defined in claim 8, wherein said hydrogenation reaction is conducted for a time of 2 to 96 hours.25. The process as defined in claim 8, wherein said hydrogenation reaction is conducted for a time of 5 to 48 hours.26. The process as defined in claim 8, wherein said hydrogenation reaction is conducted at a temperature of 30 to 40° C. for a time of 5 to 48 hours.27. The crystal as defined in claim 10, which has a purity of at least 97% by weight.28. The crystal as defined in claim 10, which has a melting point of at lowest 145° C.
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