(z)-solanone, and preparation process and use thereof

US11198665B1 · kind B1 · utility

Assignee

• CHINA TOBACCO YUNNAN INDUSTRIAL CO., LTD. · CN

Inventors

• Sheng LEI · Honghe, CN
• Zhihua Liu · Beijing, CN
• Kai Wang · Longbeilingcun, CN
• Zhenjie Li · Eastvale, US
• Deshou Mao · Kunming, CN
• Kunmiao Wang · Kunming, CN
• Li Gao · Nanjing, CN
• Lei Fu · Hamilton, CA
• Yipeng Zhang · Longbeilingcun, CN
• Wei ZHE · Kunming, CN
• Ying Yang · Bedford, US
• Qianghui Zhou · Kunming, CN

Key dates

• Filing date: Jun 1, 2020
• Grant date: Dec 14, 2021
• Expiry date: Jun 1, 2040

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/09
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A (Z)-solanone has the steric formula of:or with the name of (S,Z)-5-isopropyl-8-methyl-6,8-diene-2-one or (R,Z)-5-isopropyl-8-methyl-6,8-diene-2-one. A process for the preparation of the (Z)-type solanone and the use thereof in flavoring of cigarette shred are further disclosed. The process includes the following steps: (1) reacting isopentanal and methyl vinyl ketone, under the action of a catalyst and a co-catalyst, to give (S)-2-isopropyl-5-carbonylhexanal or (R)-2-isopropyl-5-carbonylhexanal; (2) reacting the (S)-2-isopropyl-5-carbonylhexanal or the (R)-2-isopropyl-5-carbonylhexanal obtained in step (1) with (iodomethyl)triphenylphosphonium iodide, to give (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or (R,Z)-7-iodo-5-isopropyl-6-ene-2-one; and (3) reacting the (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or the (R,Z)-7-iodo-5-isopropyl-6-ene-2-one obtained in step (2) with pinacol isopropenylborate in the presence of a catalyst to give the (Z)-solanone.