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US 2021/0403406 A1Published application
Process for preparing 2,6-dialkylphenylacetic acids
AssigneeBayer Aktiengesellschaft
InventorsThomas HIMMLER, Dirk BROHM, Wahed Ahmed MORADI
Life of this patent
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Abstract
The invention relates to a multi-stage process for preparing 2,6-dialkylphenylacetic acids of the general formula (I) by reacting 2,6-dialkylbromobenzenes with (1) magnesium, (2) a formamide, (3) an acid, (4) hydrogenation of the benzaldehyde obtained, (5) activation of the benzyl alcohol obtained, (6) cyanation of the activated benzyl alcohol and (7) hydrolysis of the nitrile obtained.
Claims16
Process for preparing compounds of formula (I)
- in which
- R1 and R2 independently of one another represent C1-C6-alkyl,
- and
- R3 represents hydrogen, C1-C6-alkyl, fluorine or chlorine,
- (1) reacting one or more compounds of formula (II)
- in which R1, R2 and R3 have the definitions given above,
- with magnesium in the presence of a solvent to give one or more compounds of formula (III),
- in which R1, R2 and R3 have the meanings given above;
- (2) the one or more compounds of formula (III) are reacted with one or more compounds of formula (IV)
- in which
- R4 and R5 independently of one another represent C1-C6-alkyl or together represent —(CH2)2—X—(CH2)2—, wherein
- X represents CH2, oxygen or sulfur,
- to give a compound of formula (V)
- in which R1, R2, R3, R4 and R5 have the definitions given above;
- (3) the one or more compounds of formula (V) are reacted by hydrolysis under acidic conditions to give one or more compounds of formula (VI)
- in which R1, R2 and R3 have the definitions given above,
- (4) one or more compounds of formula (VI) are hydrogenated to give one or more compounds of formula (VII)
- in which R1, R2 and R3 have the definitions given above,
- in the presence of a catalyst;
- (5) one or more compounds of formula (VII) are reacted to give one or more compounds of formula (VIII)
- in which R1, R2 and R3 have the definitions given above, and
- Y represents chlorine, bromine, OSO2Me, OSO2(4-Me-Ph) or OSO2CF3,
- (6) one or more of the compounds of formula (VIII) are reacted with a cyanide of formula (IX)
- MCN (IX),
- in which
- M represents lithium, sodium or potassium,
- to give one or more compounds of formula (X)
- in which R1, R2 and R3 have the definitions given above;
- (7) one or more of the compounds of formula (X) are hydrolysed under acidic or basic conditions to give one or more compounds of formula (I)
- in which R1, R2 and R3 have the definitions given above.
27 more elements
Compound of formula (V)
- in which R1 and R2 independently of one another represent C1-C6-alkyl,
- and
- R3 represents hydrogen, C1-C6-alkyl, fluorine or chlorine,
- R4 and R5 independently of one another represent C1-C6-alkyl or together represent —(CH2)2—X—(CH2)2—, wherein
- X represents CH2, oxygen or sulfur,
- excluding the compound of formula (V) in which R1 and R2 represent methyl, R3 represents hydrogen and R4 and R5 represent methyl.
3 more elements
Compound of formula (VIII)
- in which R1 and R2 independently of one another represent C1-C6-alkyl,
- and
- R3 represents hydrogen, C1-C6-alkyl, fluorine or chlorine,
- and
- Y represents OSO2Me, OSO2(4-methylphenyl) or OSO2CF3,
- excluding the following compounds
3 more elements
Dependencies are inferred from the claim text.