Claims
- 1. In the process of preparing a compound corresponding to the formula ##STR38## wherein: R.sub.1 and R.sub.2 are each independently lower alkyl; and ##STR39## wherein: n is 0, 1, 2 or 3; and
- X is nitro, cyano, halo, lower alkyl, lower alkoxy, lower alkylthio or lower alkylsulfinyl, with the proviso that R does not bear more than one nitro group, lower alkylthio group or lower allkylsulfinyl group; by reacting in an inert liquid reaction medium and under neutral or alkaline conditions (a) a compound corresponding to the formula
- R-O.sup..crclbar. M.sup..sym. or M.sup..sym..spsp..crclbar. O--C.sub.6 H.sub.4 --S--C.sub.6 H.sub.4 --O.sup..crclbar. M.sup..sym.
- with (b) a compound corresponding to the formula ##STR40## wherein M is an alkali metal and R, R.sub.1 and R.sub.2 have the aforesaid meaning; the improvement consisting of conducting the process in the presence of a small but catalytic amount of (1) a quaternary ammonium salt having a mininum solubility of at least 1 weight percent in the liquid reaction medium at 25.degree. C and (2) a diazole corresponding to the formula ##STR41## wherein R.sub.3 is hydrogen or alkyl of 1 to 6 carbon atoms.
- 2. The process defined in claim 1 wherein (1) is an ammonium salt of the formula
- R.sub.1 'R.sub.2 'R.sub.3 ' R.sub.4 'N.sup..sym. A.sup..crclbar.
- wherein R.sub.1 '-R.sub.4 ' are each independently hydrocarbyl groups of from 1 to about 12 carbon atoms, or R.sub.1 ' is joined with R.sub.2 ' to form a 5- or 6-membered heterocyclic having at least one quaternized nitrogen atom within the ring and may additionally contain one non-adjacent atom of nitrogen, oxygen or sulfur within the ring; and A.sup..crclbar. is a neutralizing anion.
- 3. The process defined in claim 2 wherein (1) is benzyltrimethylammonium chloride or bromide, or benzyltriethylammonium chloride or bromide.
- 4. The process defined in claim 3 wherein (1) is benzyltriethylammonium chloride.
- 5. The process defined in claim 1 wherein (2) is ##STR42## wherein R.sub.3 has the aforesaid meaning.
- 6. The process defined in claim 1 wherein R.sub.3 is hydrogen, methyl or ethyl.
- 7. The process defined in claim 6 wherein R.sub.3 is methyl.
- 8. The process defined in claim 1 wherein the mole ratio of (1) to (2) is from about 1:20 to about 20:1.
- 9. The process defined in claim 8 wherein said ratio is from about 1:2 to about 2:1.
- 10. The process defined in claim 1 wherein the combined amount of (1) and (2) is from about 0.25 to about 20 mole percent, based on the combined moles of (a) and (b).
- 11. The process defined in claim 10 wherein the combined amount of (1) and (2) is from about 0.5 to about 2 mole percent.
- 12. The process defined in claim 1 wherein said process is conducted in an agitated 2-phase solvent system consisting of an inert water-immiscible organic liquid and water.
- 13. The process defined in claim 1 wherein R.sub.1 and R.sub.2 are methyl or ethyl.
- 14. The process defined in claim 13 wherein R is ##STR43##
- 15. The process defined in claim 14 wherein (1) is benzyltrimethylammonium chloride or bromide or benzyltriethylammonium chloride or bromide.
- 16. The process defined in claim 15 wherein (2) is ##STR44## wherein R.sub.3 is hydrogen methyl or ethyl.
- 17. The process defined in claim 16 wherein said process is conducted in an agitated 2-phase solvent system consisting of an inert water-immiscible organic liquid and water.
CROSS-REFERENCE TO RELATED APPLICATION
This is a division of application Ser. No. 600,542, filed July 31, 1975, now U.S. Pat. No. 4,028,439 grant 6/7/77, which in turn is a division of Ser. No. 354,040, filed Apr. 24, 1973, now U.S. Pat. No. 3,917,621 granted 11/4/75, which in turn is a continuation-in-part of application Ser. No. 229,171, filed Feb. 24, 1972, now abandoned.
US Referenced Citations (6)
Divisions (2)
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Number |
Date |
Country |
Parent |
600542 |
Jul 1975 |
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Parent |
354040 |
Apr 1973 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
229171 |
Feb 1972 |
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