Process for preparing compounds derived from 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one
AssigneeL'oreal
InventorsPatricio Guerreiro, Thibaut Martin, Thierry Bordier, Lucie Leseurre
Life of this patent
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Abstract
The present invention relates to a process for preparing one or more compounds derived from 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one corresponding to formula (I), as described below, and the optical isomers or geometrical isomers thereof, and also the salts thereof with alkaline agents, and/or the solvates thereof, such as the hydrates. The invention also relates to one or more particular compounds derived from 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one corresponding to formula (I′) as defined below.
Claims24
Process for preparing at least one compound of formula (I) below:
- in which formula (I):
- R1 represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 6 carbon atoms;
- preferably R1 represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl;
- R2 represents a hydrogen atom or a C2-C4 alkyl group, such as methyl or ethyl;
- preferably R2 represents a hydrogen atom;
- R3 represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 12 atoms, optionally substituted with an aryl group;
- the aryl group preferably being a phenyl group optionally substituted with one or more groups chosen from hydroxyl, C1-C4 alkyl group, C1-C4 alkoxy group and combinations thereof;
- preferably R3 represents a C1-C6 alkyl group;
- preferably a C1-C4 alkyl group;
- and also one of the optical isomers or geometrical isomers thereof, and/or one of the salts thereof with an organic or inorganic acid or base, and/or one of the solvates thereof, such as the hydrates;
- said process taking place according to the following synthesis scheme (1):
- in which synthetic pathway (1):
- X represents a heteroatom chosen from oxygen and sulfur, preferably an oxygen atom,
- R1, R2 and R3 have the same meanings as in the formula (I);
- said process being characterised in that it comprises:
- at least one step (i) of reacting the compound of formula (II) in the presence of:
- at least one compound of formula (III),
- at least one (non)polar (a)protic solvent, and
- at least one alkaline agent in an excess molar amount relative to the compound of formula (II),
- in order to result in the formation of at least one precipitate including at least one compound of formula (IV), geometrical isomers thereof and/or one of the one of the salts thereof with an organic or inorganic base;
- and
- at least one step (i1) of separating the precipitate from the reaction medium of step (i), then
- at least one step (i2) of acidifying the precipitate using at least one inorganic or organic, preferably inorganic acidifying agent, before carrying out the reaction step (ii).
Compound of formula (I′) below:
- in which formula (I′):
- R1 represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 6 carbon atoms;
- preferably R1 represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl;
- R2 represents a hydrogen atom or a C2-C4 alkyl group, such as methyl or ethyl;
- preferably R2 represents a hydrogen atom;
- R3 represents a branched, saturated or unsaturated hydrocarbon group comprising from 1 to 12 atoms;
- preferably R3 represents a branched, saturated or unsaturated hydrocarbon group comprising from 3 to 12 carbon atoms;
- more preferably R3 represents a branched C1-C6 alkyl group, more preferentially R3 represents a branched C3-C6 alkyl group;
- especially R3 represents a branched C3-C4 alkyl group, in particular a branched C4 alkyl group;
- and also one of the optical isomers or geometrical isomers thereof, and/or one of the salts thereof with an organic or inorganic acid or base, and/or one of the solvates thereof, such as the hydrates.
Compound of formula (IV′) below, the reduced form (IV′red) thereof, and also one of the optical isomers or Z/Z, Z/E, L/Z and L/E geometrical isomers thereof, and/or one of the salts thereof with an organic or inorganic acid or base, and/or one of the solvates thereof, such as the hydrates:
- in which formula (IV′) or (IV′red):
- R1 represents a linear or branched, saturated or unsaturated hydrocarbon group comprising from 1 to 6 carbon atoms;
- preferably R1 represents a C1-C4 alkyl group, more preferentially a C2-C4 alkyl group, such as ethyl;
- R2 represents a hydrogen atom or a C2-C4 alkyl group, such ethyl;
- preferably R2 represents a hydrogen atom.
Dependencies are inferred from the claim text.