Synthesis of peretinoin

Patent metadata

Field	Value
Publication number	US-9296677-B2
Application number	US-201113877241-A
Country	US
Kind code	B2
Filing date	Sep 29, 2011
Priority date	Oct 1, 2010
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

The present invention relates to a new and improved synthesis of peretinoin.

First claim

The invention claimed is:

1. A process for the production of a peretinoin compound of formula (IIIa):

wherein the process comprises the following steps:
(a) reacting a compound of formula (I) or (I′),

wherein
R 2 is substituted phenyl, unsubstituted phenyl, —(CH2)3-OH, or —(CH2)3-CH3,
R′ 2 is OC 1 -C 4 alkyl, and
X is a halogen ion,
with a compound of formula (II)

wherein R 1 is H, and

(b) forming the compound of formula (I) or formula (I′) by reacting a compound of formula (IV):

with HX, wherein X is I or Br, and
a compound of formula (V) or formula (V′)

wherein
R 2 is phenyl, —(CH 2 ) 3 —OH, or —(CH 2 ) 3 —CH 3 , and
R′ 2 is OC 1 -C 4 alkyl, wherein

the reactions of steps (a) and (b) are carried out in a one-pot-reaction in the presence of the same inert organic solvent.

Assignees

• Beumer Raphael
• Dsm Ip Assets Bv

Inventors

• Beumer Raphael

Classifications

• C07F9/5428

  Acyclic unsaturated phosphonium compounds · CPC title

• C07F9/5022

  Aromatic phosphines (P-C aromatic linkage) · CPC title

• C07C67/343

  by increase in the number of carbon atoms · CPC title

• C07F9/5442

  Aromatic phosphonium compounds (P-C aromatic linkage) · CPC title

• C07F9/4015

  Esters of acyclic unsaturated acids · CPC title