Provided are a tricyclodecane dimethanol composition, in which a ratio of structural isomers is controlled, and a preparation method thereof.

An aryl-substituted alkanal compound having a molecular weight of less than 300 g/mol and which bears a substituent on the aryl ring ortho to a substituent bearing the aldehyde functionality. Said compounds are useful as perfume ingredients in personal care and household care products.

An aryl-substituted alkanal compound having a molecular weight of less than 300 g/mol and which bears a substituent on the aryl ring ortho to a substituent bearing the aldehyde functionality. Said compounds are useful as perfume ingredients in personal care and household care products.

The present invention is able to provide a bifunctional compound represented by formula (1).

##STR00001##

(In the formula, R.sub.1 represents COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7, COOC.sub.4H.sub.9 or CHO; and R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5.)

The present invention is able to provide a bifunctional compound represented by formula (1).

##STR00001##

(In the formula, R.sub.1 represents COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7, COOC.sub.4H.sub.9 or CHO; and R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5.)

The present invention is able to provide a bifunctional compound represented by formula (1).

##STR00001##

(In the formula, R.sub.1 represents COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7, COOC.sub.4H.sub.9 or CHO; and R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5.)

A method for producing a bifunctional compound of formula (3) ##STR00001## wherein R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5, the method comprising reducing a bifunctional compound of formula (1): ##STR00002## wherein R.sub.1 represents COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7, COOC.sub.4H.sub.9, or CHO; and R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5, provided that when R.sub.1 represents CHO, R.sub.2 represents C.sub.2H.sub.5, in the presence of a catalyst having hydrogenation activity and hydrogen.

A method for producing a bifunctional compound of formula (3) ##STR00001## wherein R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5, the method comprising reducing a bifunctional compound of formula (1): ##STR00002## wherein R.sub.1 represents COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7, COOC.sub.4H.sub.9, or CHO; and R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5, provided that when R.sub.1 represents CHO, R.sub.2 represents C.sub.2H.sub.5, in the presence of a catalyst having hydrogenation activity and hydrogen.

A method for producing a bifunctional compound of formula (3) ##STR00001## wherein R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5, the method comprising reducing a bifunctional compound of formula (1): ##STR00002## wherein R.sub.1 represents COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7, COOC.sub.4H.sub.9, or CHO; and R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5, provided that when R.sub.1 represents CHO, R.sub.2 represents C.sub.2H.sub.5, in the presence of a catalyst having hydrogenation activity and hydrogen.

The present invention is able to provide a bifunctional compound represented by formula (I).

##STR00001## (In the formula, R.sub.1 represents COOCH.sub.3, COOC.sub.2H.sub.5, COOC.sub.3H.sub.7, COOC.sub.4H.sub.9 or CHO; and R.sub.2 represents H, CH.sub.3 or C.sub.2H.sub.5.)