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US 6,184,394 B2Granted
Process for the preparation of 3-furoate esters and novel intermediate compounds
AssigneeEastman Chemical Company
InventorStephen Neal Falling
Life of this patent
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Abstract
Disclosed is a two-step process wherein a 4-acyl-2,3-dihydrofuran is converted to a 2-alkoxy-3-acyl-3-halotetrahydorfuran which then is contacted with an strong base to produce an alkyl 3-furoate. Also disclosed are novel 2-alkoxy-3-acyl-3-halotetrahydrofuran intermediates.
Claims13
Process for preparing a compound having the formula:
- which comprises the steps of:
- (1) contacting a compound having the formula:
- with a halogenating agent in the presence of an alkanol to obtain an intermediate compound having the formula:
- and
- (2) contacting intermediate compound (III) with a strong base to produce compound (I) provided that step (2) is carried out in the presence of a source of alkoxide when R2 is perhaloalkyl;
- wherein R1 is alkyl;
- R2 is perhaloalkyl or alkoxy;
- R3 is alkyl;
- and X is halogen.
6 more elements
Process for preparing a compound having the formula:
- which comprises the steps of:
- (1) contacting a compound having the formula:
- with a halogenating agent selected from bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, chlorine, 1,3-dichloro-5,5-dimethyl-hydantoin and N-chlorosuccinimide in the presence of an alkanol having up to about 4 carbon atoms to obtain an intermediate compound having the formula:
- and
- (2) contacting intermediate compound (III) with a sodium or potassium alkoxide having up to about 4 carbon atoms to produce compound (I);
- wherein R1 is alkyl of up to about 4 carbon atoms;
- R2 is perhalomethyl;
- R3 is alkyl having up to about 4 carbon atoms;
- and X is chloro or bromo.
6 more elements
A compound having the formula:
- wherein R2 is perhaloalkyl or alkoxy;
- R3 is alkyl;
- and X is halogen.
Dependencies are inferred from the claim text.