Diester compound having a dimethylcyclobutane ring, a process for preparing the same, and a process for preparing dimethylcyclobutane compound derived from the diester compound

Patent metadata

Field	Value
Publication number	US-12281069-B2
Application number	US-202217737502-A
Country	US
Kind code	B2
Filing date	May 5, 2022
Priority date	Jul 17, 2019
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

Abstract

The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R 1 and R 2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R 1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R 2 and R 3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring.

First claim

The invention claimed is:

1. A process for preparing an isopropenyl dimethylcyclobutane compound of formula (6):

wherein X 3 is selected from the group consisting of a hydroxyl group, an acyloxy group having 1 to 10 carbon atoms including a carbon atom of a carbonyl group, an alkoxycarbonyloxy group having 2 to 10 carbon atoms including a carbon atom of a carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, a silyloxy group having 3 to 20 carbon atoms, and a halogen atom,
the process comprising:
subjecting a diester compound of formula (1), having a dimethylcyclobutane ring:

wherein R 1 and R 2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms,
to a reduction reaction to produce a diol compound of formula (4), having a dimethylcyclobutane ring:

changing a hydroxyl group in the moiety of HOCH 2 —(CH 3 )C═ in the diol compound of formula (4) and optionally a hydroxyl group in the moiety of —CH 2 OH in the diol compound of formula (4) to X 1 and X 2 , respectively, to prepare a dimethylcyclobutane compound of formula (5):

wherein X 1 is selected from the group consisting of an acyloxy group having 1 to 10 carbon atoms including a carbon atom of a carbonyl group, an alkoxycarbonyloxy group having 2 to 10 carbon atoms including a carbon atom of a carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, a silyloxy group having 3 to 20 carbon atoms, a trialkylphosphonio group having 3 to 30 carbon atoms, a triarylphosphonio group having 12 to 30 carbon atoms, and a halogen atom; and X 2 is selected from the group consisting of a hydroxyl group, an acyloxy group having 1 to 10 carbon atoms including a carbon atom of a carbonyl group, an alkoxycarbonyloxy group having 2 to 10 carbon atoms including a carbon atom of a carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, a silyloxy group having 3 to 20 carbon atoms, and a halogen atom; and
subjecting the dimethylcyclobutane compound of formula (5) to a reduction reaction to produce the isopropenyl dimethylcyclobutane compound of formula (6).

Assignees

• Shinetsu Chemical Co

Inventors

• Ishibashi Naoki
• Nagae Yusuke
• Kinsho Takeshi

Classifications

• C07C69/74 Primary

  Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring · CPC title

• C07C67/40

  by oxidation of primary alcohols · CPC title

• C07C67/14

  from carboxylic acid halides · CPC title

• C07C67/10

  by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond (preparation from carboxylic acid halides C07C67/14) · CPC title

• C07C29/62

  by introduction of halogen; by substitution of halogen atoms by other halogen atoms · CPC title