Process for preparing (9e, 11z)-9,11-hexadecadienal

• US 10,618,862 B2
• Filed: 04/18/2019
• Issued: 04/14/2020
• Est. Priority Date: 04/18/2018
• Status: Active Grant

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Watanabe, Tomohiro, Miyake, Yuki, Kinsho, Takeshi, Nagae, Yusuke
• Primary Examiner(s): Witherspoon, Sikarl A
• Application Number:
  US16/388,124
• Publication Number:
  US 20190322605A1
• Time in Patent Office: 362 Days
• CPC Class Codes: C07B 2200/09 Geometrical isomers
• CPC Class Codes: C07C 29/58 by elimination of halogen, e.g. by hydrogenolysis, splitting-off C07C29/124 takes precedence
• CPC Class Codes: C07C 41/50 by reactions producing groups
• CPC Class Codes: C07C 43/303 having acetal carbon atoms bound to acyclic carbon atoms
• CPC Class Codes: C07C 45/515 the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group cyclic acetals or ketals C07C45/59, C07C45/60
• CPC Class Codes: C07C 47/21 with only carbon-to-carbon double bonds as unsaturation

Abstract

An efficient process for preparing (9E,11Z)-9,11-hexadecadienal of formula (4)

is provided. The process includes at least steps of: conducting a nucleophilic substitution reaction between an (8E,10Z)-8,10-pentadecadienyl magnesium halide derived from an (8E,10Z)-1-halo-8,10-pentadecadiene of (1):

and an orthoformate ester (2)

to thereby prepare a (9E, 11Z)-1,1-dialkoxy-9, 11-hexadecadiene (3):

and hydrolyzing the (9E, 11Z)-1,1-dialkoxy-9,11-hexadecadiene (3) to obtain (9E, 11Z)-9,11-hexadecadienal (4).

Claims

1. A process for preparing (9E,11Z)-9,11-hexadecadienal of the following formula (4):

2. A process for preparing (9E,11Z)-9,11-hexadecadienal of the following formula (4):