Claims
- 1. A process for preparing an .alpha.-arylalkanoic acid of the formula ##STR16## or an ester, orthoester or amide thereof wherein Ar is an aryl moiety, and R.sub.1 is lower alkyl having 1-8 carbon atoms inclusive or cycloalkyl having 3-7 carbon atoms inclusive, which comprises:
- contacting an .alpha.-halo alkyl aryl ketone of the formula ##STR17## wherein Ar and R.sub.1 are as defined above and X is halo with an alkali metal aryloxide or alkoxide to form the .alpha.-hydroxy ketal of the formula ##STR18## wherein R.sub.2 and R.sub.3 are the aryl or alkyl residues of the aryloxide or alkoxide groups,
- contacting the .alpha.-hydroxy ketal with a source of sulfonyl ion to form the corresponding sulfonate ester, and maintaining the sulfonate ester in contact with a protic or dipolar, aprotic solvent for a time sufficient to form the corresponding .alpha.-arylalkanoic acid or ester, orthoester or amide thereof and
- optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding acid.
- 2. The process of claim 1 wherein the source of sulfonyl ion is an alkylsulfonyl or an arylsulfonyl halide.
- 3. The process of claim 2 wherein R.sub.2 and R.sub.3 are methyl and the source of sulfonyl ion is methanesulfonyl chloride, p-toluenesulfonyl chloride or benzenesulfonyl chloride.
- 4. The process of claim 3 wherein Ar is 6-methoxy-2-naphthyl and R.sub.1 is methyl.
- 5. The process of claim 3 wherein Ar is 4-isobutylphenyl and R.sub.1 is methyl.
- 6. The process of claim 3 wherein Ar is 3-phenoxyphenyl and R.sub.1 is methyl.
- 7. A compound of the formula ##STR19## wherein Ar.sub.1 is phenyl, phenoxyphenyl, naphthyl or biphenyl, optionally substituted with lower alkyl, lower alkoxy or halo, R.sub.1, R.sub.7 and R.sub.8 are lower alkyl having 1-4 carbon atoms inclusive, and Y is an alkyl, cycloalkyl, alkenyl, alkynyl, aryl or aralkyl sulfonyloxy group.
- 8. The compound of claim 7 wherein Ar.sub.1 is 6-methoxy-2-naphthyl.
- 9. The compound of claim 8 which is 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate.
- 10. The compound of claim 8 which is 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate.
- 11. The compound of claim 8 which is 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl benzenesulfonate.
- 12. The compound of claim 7 wherein Ar.sub.1 is 4-isobutylphenyl.
- 13. The compound of claim 12 which is 1-(4-isobutylphenyl)-1,1-dimethoxyprop-2-yl methanesulfonate.
- 14. The compound of claim 7 wherein Ar.sub.1 is 1,1-dimethoxy-1-(3-phenoxyphenyl)propan-2-ol.
- 15. The compound of claim 14 which is 1,1-dimethoxy-1-(3-phenoxyphenyl)prop-2-yl methane-sulfonate.
- 16. A compound of the formula ##STR20## wherein Ar.sub.1 is phenoxyphenyl, naphthyl or biphenyl, optionally substituted with lower alkyl, lower alkoxy or halo and R.sub.1, R.sub.7 and R.sub.8 are lower alkyl having 1-4 carbon atoms inclusive.
- 17. The compound of claim 16 wherein Ar.sub.1 is 6-methoxy-2-naphthyl.
- 18. The compound of claim 17 which is 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol.
- 19. The compound of claim 16 wherein Ar.sub.1 is 3-phenoxyphenyl.
- 20. The compound of claim 19 which is 1,1-dimethoxy-1-(3-phenoxyphenyl)propan-2-ol.
- 21. The compound which is 1-(4-isobutylphenyl)-1,1-dimethoxypropan-2-ol.
Parent Case Info
This is a division of application Ser. No. 502,036 filed June 7, 1983 which is a continuation of application Ser. No. 259,119 filed Apr. 30, 1981 now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4539420 |
Tsuchihashi et al. |
Sep 1985 |
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Divisions (1)
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Number |
Date |
Country |
Parent |
502036 |
Jun 1983 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
259119 |
Apr 1981 |
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