Process for the preparation of thiophene ethers
First Claim
1. A thiophene ether of the formula I ##STR6## in which R1 denotes a straight-chain or branched C7 -C18 -alkoxy radical, a C4 -C18 alkenyloxy radical, a C3 -C12 -alkynyloxy radical, a C5 -C6 -cycloalkoxy radical, a phenyl-C1 -C4 -alkoxy radical, a radical of the formula II
in which n is 2 to 6 and X denotes a halogen atom, a hydroxyl, carboxylic ester, --SO3 Me (Me is an alkali metal or --N+R45 where R5 is H or alkyl), nitro, cyano, carboxamide, --OCH3, --OC2 H5 or --(OCH2 Ch2)m -- OCH3 group where m is 1 to 3, a quaternary ammonium group or a --P(O)(OR4)2 group where R4 is H or C1 -C4 -alkyl, or denotes a radical of glycolic acid, thioglycolic acid, lactic acid or the ester of these acids,R2 denotes R1 or a hydrogen atom, a C1 -C12 -alkyl group or an aryl radical,R3 denotes a hydrogen atom, a C1 -C6 -alkyl group or a C4 -C6 -alkoxy group.
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Abstract
Thiophene ethers having relatively large side chains can be easily obtained by reacting 2-, 3-, 2,3-, 2,4- or 3,4-C1 -C3 -alkoxythiophenes in the presence of an acid catalyst with a compound containing an OH group. The novel thiophene ethers are suitable as monomers for electrically conducting polymers.
5 Citations
8 Claims
- 1. A thiophene ether of the formula I ##STR6## in which R1 denotes a straight-chain or branched C7 -C18 -alkoxy radical, a C4 -C18 alkenyloxy radical, a C3 -C12 -alkynyloxy radical, a C5 -C6 -cycloalkoxy radical, a phenyl-C1 -C4 -alkoxy radical, a radical of the formula II
- space="preserve" listing-type="equation">--O(CH.sub.2).sub.n --X (II)
in which n is 2 to 6 and X denotes a halogen atom, a hydroxyl, carboxylic ester, --SO3 Me (Me is an alkali metal or --N+R45 where R5 is H or alkyl), nitro, cyano, carboxamide, --OCH3, --OC2 H5 or --(OCH2 Ch2)m -- OCH3 group where m is 1 to 3, a quaternary ammonium group or a --P(O)(OR4)2 group where R4 is H or C1 -C4 -alkyl, or denotes a radical of glycolic acid, thioglycolic acid, lactic acid or the ester of these acids, R2 denotes R1 or a hydrogen atom, a C1 -C12 -alkyl group or an aryl radical, R3 denotes a hydrogen atom, a C1 -C6 -alkyl group or a C4 -C6 -alkoxy group.
- 2. A process for the preparation of thiophene ethers of the formula I ##STR7## in which R1 denotes a straight-chain or branched C1 -C18 -alkoxy radical, a C3 -C18 -alkenyloxy radical, a C3 -C12 -alkynyloxy radical, a C5 -C6 -cycloalkoxy radical, a phenyl-C1 -C4 -alkoxy radical, a radical of the formula II
- space="preserve" listing-type="equation">--O(CH.sub.2).sub.n --X (II)
in which n denotes 2 to 6 and X denotes a halogen atom, a hydroxyl, carboxylic ester, --SO3 Me (Me is an alkali metal or --N+ R45 where R5 is H or alkyl), nitro, cyano, carboxamide, --OCH3, --OC2 H5 or --(OCH2 CH2)m -- OCH3 group where m is 1 to 3, a quaternary ammonium group or a --P(O)(OR4)2 group where R4 is H or C1 -C4 -alkyl, or denotes a radical of glycolic acid, thioglycolic acid, lactic acid or the ester of these acids, R2 denote R1 or a hydrogen atom, a C1 -C12 -alkyl group or an aryl radical, R3 denotes a hydrogen atom, a C1 -C6 -alkyl group or a C4 -C6 -alkoxy group, which comprises heating a 2-, 3-, 2,3-, 2,4- or 3,4-C1 -C3 -alkoxythiophene together with a compound containing an OH group of the formula
space="preserve" listing-type="equation">R.sup.1 --OH (III)in which R1 has the abovementioned meaning, in the presence of an acid catalyst in an amount of 1 to 10 moles %, relative to the amount of the alkoxythiophene, for 50 to 300 minutes to a temperature of about 100°
to 150°
C. and separating off the resulting C1 -C3 -alcohol, wherein the acid catalyst is H2 SO4, NaHSO4, H3 PO4, HBF4, p-toluene-sulfonic acid or a polymeric sulfonic acid.- View Dependent Claims (3, 4, 5, 6, 7, 8)
Specification
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- Resources
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Current AssigneeHoechst Aktiengesellschaft (Sanofi )
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Original AssigneeHoechst Aktiengesellschaft (Sanofi )
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InventorsLitterer, Heinz, Wegener, Peter, Feldhues, Michael
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Primary Examiner(s)SIEGEL, ALAN M
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Application NumberUS07/308,893Time in Patent Office481 DaysField of Search549/62, 549/6, 549/65, 549/66, 568/630US Class Current549/6CPC Class CodesC07D 333/32 Oxygen atomsC07F 9/655345 the sulfur atom being part ...H01B 1/127 comprising five-membered ar...
