Claims
- 1. A method for the preparation of phenylacrylic esters of the formula II ##STR12## wherein R.sup.1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, and R.sup.2 is a hydrogen or methyl group;
- or R.sup.1 and R.sup.2 together form a methylenedioxy group;
- and R.sup.3 is a lower alkyl group, which method comprises:
- (1) condensing the appropriately substituted phenol acetic ester of formula V ##STR13## with a di(lower alkyl)oxalate in the presence of a basic catalyst, to produce a solution of an enolate salt of formula IV ##STR14## wherein R is a lower alkyl group and M is an alkali metal, (2) acidifying the solution of the salt IV to give the corresponding phenyloxaloacetate III ##STR15## (3) reacting the compound III with formaldehyde under alkaline conditions to give the corresponding phenyl hydroxymethyl acetate which spontaneously dehydrates to the ester II,
- each of the steps (1), (2) and (3) being carried out at room temperature.
- 2. A method as claimed in claim 1 wherein the basic catalyst is an alkali metal alcholate.
- 3. A method as claimed in claim 2 wherein the alkali metal is sodium.
- 4. A method as claimed in claim 1 wherein R.sup.1 is an ethoxy group and R.sup.2 is hydrogen.
- 5. A method as claimed in claim 1 wherein R.sup.1 is nitro and R.sup.2 is hydrogen.
- 6. A method as claimed in claim 1 wherein R.sup.1 is chloro and R.sup.2 is hydrogen.
- 7. A method as claimed in claim 1 wherein R.sup.1 is bromo and R.sup.2 is hydrogen.
- 8. A method as claimed in claim 1 wherein R.sup.1 is methoxy and R.sup.2 is hydrogen.
- 9. A method as claimed in claim 1 wherein R.sup.1 and R.sup.2 form methylenedioxy.
- 10. A method as claimed in claim 1 wherein R.sup.1 is ethylthio and R.sup.2 is hydrogen.
Priority Claims (1)
Number |
Date |
Country |
Kind |
PC4078 |
Nov 1975 |
AUX |
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Parent Case Info
This is a division of application Ser. No. 742,575, filed Nov. 17, 1976, U.S. Pat. No. 4,220,591.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3442935 |
Pine |
May 1969 |
|
3803254 |
Hattori et al. |
Apr 1974 |
|
3804899 |
Ebnother et al. |
Apr 1974 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
655700 |
Aug 1979 |
SUX |
Divisions (1)
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Number |
Date |
Country |
Parent |
742575 |
Nov 1976 |
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