Process for producing 3,4-dihydrocoumarin derivatives

摘要

For producing a 3,4-dihydrocoumarin compound represented by formula (II): CHEM wherein R1 and R4 each is a hydrogen atom or a methyl or ethyl group, provided that at least two of R1 to R4 represents hydrogen, (1) a 3-(2-cyclohexanoyl)propionic acid ester compound represented by formula (I): CHEM where R1 to R4 are as above and R5 is C1-4 alkyl, is heated in the presence of at least one solid metal catalyst selected from Pt, Pd, Ir, Rh and Ni; thereby to allow the compound of formula (I) to undergo ring formation and dehydrogenation to yield the 3,4-dihydrocoumarin compound (II) and, as a by-product, a coumarin compound represented by formula (III): CHEM (2) the coumarin compound (III) is partially hydrogenated, while the coumarin compound is kept unseparated from the reaction mixture that has undergone the ring formation and dehydrogenation, by adding a catalyst as defined above, to the reaction mixture, or bringing the reaction mixture into contact with oxygen to activate the catalyst used in the ring formation and dehydrogenation; and then bringing the resulting reaction mixture into contact with hydrogen thereby to partially hydrogenate the coumarin compound (III) so as to convert the coumarin compound (III) to the 3,4-dihydrocoumarin compound (II).