US 12,281,069 B2
Diester compound having a dimethylcyclobutane ring, a process for preparing the same, and a process for preparing dimethylcyclobutane compound derived from the diester compound
Naoki Ishibashi, Joetsu (JP); Yusuke Nagae, Joetsu (JP); and Takeshi Kinsho, Joetsu (JP)
Assigned to Shin-Etsu Chemical Co., Ltd., Tokyo (JP)
Filed by Shin-Etsu Chemical Co., Ltd., Tokyo (JP)
Filed on May 5, 2022, as Appl. No. 17/737,502.
Application 17/737,502 is a division of application No. 16/930,578, filed on Jul. 16, 2020, granted, now 11,352,312.
Claims priority of application No. 2019-132129 (JP), filed on Jul. 17, 2019; and application No. 2020-067072 (JP), filed on Apr. 2, 2020.
Prior Publication US 2022/0259136 A1, Aug. 18, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 67/42 (2006.01); C07C 17/013 (2006.01); C07C 29/147 (2006.01); C07C 29/62 (2006.01); C07C 67/10 (2006.01); C07C 67/14 (2006.01); C07C 67/40 (2006.01); C07C 69/74 (2006.01)
CPC C07C 67/42 (2013.01) [C07C 17/013 (2013.01); C07C 29/147 (2013.01); C07C 29/62 (2013.01); C07C 67/10 (2013.01); C07C 67/14 (2013.01); C07C 67/40 (2013.01); C07C 69/74 (2013.01); C07C 2601/04 (2017.05)] 1 Claim
 
1. A process for preparing an isopropenyl dimethylcyclobutane compound of formula (6):

OG Complex Work Unit Chemistry
wherein X3 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:

OG Complex Work Unit Chemistry
wherein R1 and R2 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:

OG Complex Work Unit Chemistry
changing a hydroxyl group in the moiety of HOCH2—(CH3)C═ in the diol compound of formula (4) and optionally a hydroxyl group in the moiety of —CH2OH in the diol compound of formula (4) to X1 and X2, respectively, to prepare a dimethylcyclobutane compound of formula (5):

OG Complex Work Unit Chemistry
wherein X1 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 X2 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).