Method for producing alpha-acyloxycarbonyl compound and novel alpha-acyloxycarbonyl compound

1. A method for producing an α-acyloxycarbonyl compound by an intermolecular reaction, the method comprising:

reacting a carboxylic acid and a carbonyl compound selected from the group consisting of a ketone, an aldehyde, and an ester, which comprise a hydrogen atom at the α-position, with an oxidizer, which is a hydroperoxide and a catalyst precursor, which is an iodide salt

thereby introducing an acyloxy group derived from the carboxylic acid into the α-position of the carbonyl compound.

2. The method of claim 1 , wherein the hydroperoxide is an organic hydroperoxide.

3. The method of claim 1 , wherein the hydroperoxide is employed at 1 to 5 equivalents relative to, of the carboxylic acid and the carbonyl compound, one having a smaller number of moles.

4. The method of claim 1 , wherein the iodide salt is at least one selected from the group consisting of an ammonium iodide, a phosphonium iodide, and an alkali metal iodide.

5. The method of claim 1 , wherein the iodide salt is employed at 1 to 50 mol % relative to, of the carboxylic acid and the carbonyl compound, one having a smaller number of moles.

6. The method of claim 1 , wherein at least one selected from the group consisting of an ether solvent, an ester solvent, and a nitrile solvent is employed as a reaction solvent.

7. The method of claim 1 , wherein the reaction is performed at 25° C. or more.

8. The method of claim 1 , wherein the carbonyl compound comprises a partial structure of —C(═O)—CH 2 —.

9. The method of claim 1 , wherein the reaction is performed in the presence of an amine.

10. The method of claim 1 , wherein the carboxylic acid is an unsaturated aliphatic carboxylic acid.

11. An α-acyloxycarbonyl compound of formula (1):

wherein:

Z 1 is H or CH 3 ;

wherein:

Ar is a phenyl group, a phenyl group comprising an alkyl group, or a phenyl group comprising a halogen atom;

R is an alkyl group;

X is an alkyl group or a halogen atom;

m is an integer of 0 to 4;

n is an integer of 1 to 4;

k and k′ are each an integer of 0 to 4 and k+k′ is an integer of 1 to 4; and

A is O, S, NH, NR, or CHR, wherein R is an alkyl group; and

Z 3 is H or CH 2 ═C(Z 1 )COO—.

12. The method of claim 2 , wherein the organic hydroperoxide tert-butyl hydroperoxide and cumene hydroperoxide.

13. The method of claim 12 , wherein the organic hydroperoxide is cumene hydroperoxide.

14. The method of claim 12 , wherein the organic hydroperoxide is tert-butyl hydroperoxide.

15. The method of claim 12 , wherein the hydroperoxide is employed at 1 to 5 equivalents relative to, of the carboxylic acid and the carbonyl compound, one having a smaller number of moles.

16. The method of claim 12 , wherein the hydroperoxide is employed at 1.1 to 2.5 equivalents relative to, of the carboxylic acid and the carbonyl compound, one having a smaller number of moles.

17. The method of claim 1 , wherein the iodide salt is employed at 5 to 20 mol % relative to, of the carboxylic acid and the carbonyl compound, one having a smaller number of moles.

18. The method of claim 16 , wherein the iodide salt is employed at 5 to 20 mol % relative to, of the carboxylic acid and the carbonyl compound, one having a smaller number of moles.

19. The method of claim 1 , wherein the reaction is performed at 50° C. or more.

20. The method of claim 1 , wherein the reaction is performed at 50° C. or more and 100° C. or less.