METHOD OF PRODUCING 1-(2-t-BUTYL CYCLOHEXYLOXY)-2-ALKANOL

14:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein, during said hydrogenating, a basic substance is added in the raw material mixture.

15:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 14, wherein the basic substance is at least one member selected from the group consisting of an amine, an alkali metal compound, and an alkaline earth metal compound.

16:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 14, wherein the addition amount of the basic substance is from 1 to 3,000 ppm in terms of a nitrogen atom content or a metal content relative to the 1-(2-t-butylphenyloxy)-2-alkanol represented by the formula (1).

17:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 15, wherein the amine is at least one member selected from the group consisting of ammonia, a monovalent primary amine, a monovalent secondary amine, a monovalent tertiary amine, and a polyvalent amine.

18:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 15, wherein the addition amount of the amine is from 100 to 3,000 ppm in terms of a nitrogen atom content relative to the 1-(2-t-butylphenyloxy)-2-alkanol represented by formula (1).

19:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 15, wherein the addition amount of the alkali metal compound or the alkaline earth metal compound is from 1 to 1,000 ppm in terms of a metal content relative to the 1-(2-t-butylphenyloxy)-2-alkanol represented by the formula (1).

20:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein a mass ratio of palladium in the palladium catalyst (A) and at least one of ruthenium, rhodium, platinum, and nickel in the metal catalyst (B), [(A)/(B)], is from 80/20 to 99/1.

21:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein the amount of an organic solvent in said hydrogenating is not more than 10% by mass relative to the 1-(2-t-butylphenyloxy)-2-alkanol.

22:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 21, wherein the amount of the organic solvent in said hydrogenating is 0% by mass relative to the 1-(2-t-butylphenyloxy)-2-alkanol.

23:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein the content of a trans-isomer of the 1-(2-t-butylcyclohexyloxy)-2-alkanol is 41% by mass or more.

24:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein R1 in formula (1) represents an ethyl group.

25:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein the palladium catalyst (A) is a supported catalyst supported on a carrier.

26:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 25, wherein the carrier of the palladium catalyst (A) is an inorganic carrier.

27:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein the pH of the palladium catalyst (A) is 7.0 or more and not more than 12.0.

28:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein the metal catalyst (B) is a supported catalyst supported on a carrier.

29:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein the pH of the metal catalyst (B) is 6.0 or more and not more than 12.0.

30:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein a total amount of the palladium catalyst (A) and the metal catalyst (B) is 0.01% by mass or more and not more than 10% by mass relative to the 1-(24-butylphenyloxy)-2-alkanol represented by formula (1).

31:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein a hydrogen pressure in said hydrogenating is 0.1 MPa or more and not more than 15 MPa.

32:

• The method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol according to claim 13, wherein a reaction temperature during said hydrogenating is 50° C. or higher and not higher than 300° C.