Method for producing cyclic sulfonic acid ester and intermediate thereof
View Patent ↗The present invention is directed to provide an efficient production method which is capable of not only obtaining a cyclic sulfonic acid ester (sultone) at low cost and in high yield, but also the sulfonic acid ester (sultone) stably even in a commercial scale. The present invention relates to a method for producing hydroxysultone comprising a first step where a diol having a specified structure and a thionyl halide are reacted to obtain a cyclic sulfite having a specified structure, and a second step where the cyclic sulfite is reacted with water or/and alcohol; a method for producing an unsaturated sultone having a specified structure comprising a third step where a hydroxylsultone having a specified structure is reacted with an acid halide or an acid anhydride to obtain an intermediate, subsequently the intermediate is treated with a base; as well as a cyclic sulfite having a specified structure.
1. A method for producing a compound represented by the general formula [1]:
(wherein n pieces of R 1 , n pieces of R 2 , R 3 , R 4 and R 5 represent each independently a hydrogen atom or a C1-3 alkyl group, and n represents an integer of 1 or 2) comprising a first step where a compound represented by the general formula [2]:
(wherein n pieces of R 1 , n pieces of R 2 , R 3 , R 4 and R 5 and n are same as above, and M represents an alkali metal atom) and a thionyl halide are reacted to obtain a compound represented by the general formula [3]:
(wherein X represents a halogen atom, and n pieces of R 1 , n pieces of R 2 , R 3 , R 4 and R 5 and n are same as above); and a second step where the aforementioned compound represented by the general formula [3] is reacted with water or/and alcohol.
2. The method according to claim 1 , wherein the aforementioned first step and second step are carried out continuously.
3. The method according to claim 1 , wherein R 1 is a hydrogen atom and n is 1 in the aforementioned general formulas [1] to [3].
4. A method for producing a compound represented by the general formula [4]:
(wherein R 2 , R 3 , R 4 and R 5 represent each independently a hydrogen atom or a C1-3 alkyl group) comprising a third step where a compound represented by the general formula [1′]:
(wherein R 2 , R 3 , R 4 and R 5 are same as above) obtained in claim 3 is reacted with an acid halide or an acid anhydride to obtain a compound represented by the general formula [5]:
(wherein L represents a leaving group derived from the aforementioned acid halide or acid anhydride, and R 2 , R 3 , R 4 and R 5 are same as above), subsequently the compound represented by the aforementioned general formula [5] is treated with a base.
5. The method according to claim 4 , wherein the aforementioned first step and second step to obtain the compound represented by the general formula [1′], and third step are carried out continuously.
6. The method according to claim 4 , wherein the aforementioned acid halide is a sulfonyl halide or a carboxylic halide.
7. The method according to claim 4 , wherein the aforementioned acid anhydride is a sulfonic anhydride or a carboxylic anhydride.
8. The method according to claim 4 , wherein the aforementioned acid halide or acid anhydride is methanesulfonyl chloride or acetic anhydride.
9. A compound represented by the general formula [3]:
(wherein n pieces of R 1 , n pieces of R 2 , R 3 , R 4 and R 5 represent each independently a hydrogen atom or a C1-3 alkyl group, X represents a halogen atom, and n represents an integer of 1 or 2).