Propenals substituted with a dithiane ring and processes for the preparation of these propenals

• US 5,296,611 A
• Filed: 06/12/1992
• Issued: 03/22/1994
• Est. Priority Date: 06/14/1991
• Status: Expired due to Term

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Maignan, Jean, Solladie, Guy, Berl, Valerie
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US07/897,778
• Time in Patent Office: 648 Days
• Field of Search: 549/21, 549/22
• US Class Current: 549/21
• CPC Class Codes: C07D 339/08 Six-membered rings

Abstract

Propenals of formula: ##STR1## in which formula R is H or a C₁ -C₄ thioalkyl radical, the dithiane ring being at the cis position in relation to the aldehyde function when R is H and at the trans position when R is a thioalkyl radical. The invention also relates to two processes for the preparation of these propenals.

Claims

1. Propenals of formula:

##STR39## in which formula R is hydrogen or a C₁ -C₄ thioalkyl radical, the dithiane ring being at the cis position with respect to the aldehyde function when R is H, and at the trans position when R is a thioalkyl radical.

2. Propenal according to claim 1, of cis structure and of formula:

##STR40##

3. Propenal according to claim 1, of trans structure and of formula:

##STR41##

4. Process for the preparation of the propenal according to claim 2, characterised in that ethyl β

-formylmethacrylate of cis structure and of formula;

##STR42## in which formula Et is an ethyl group, is reacted with 1,3-propanedithiol in the presence of zinc triflate so as to obtain the compound of formula;

##STR43## where Et has the same meaning as indicated above, in that this compound of formula (IV) is reduced in the presence of diisobutylaluminium hydride in order to obtain the dithianepropenol of formula;

##STR44## and in that the said compound of formula (V) is oxidised in order to obtain the cis-propenal of formula (Ia).