Process for the synthesis of phenoxyalkane derivatives

Details Process for the synthesis of phenoxyalkane derivatives Process for the synthesis of phenoxyalkane derivatives

1982-03-31

1989-06-06

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C07C 6976

Patent

active

048373559

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to a process for the synthesis of organic compounds and in particular to a process for the synthesis of (4-hydroxyphenoxy)alkane derivatives.


BACKGROUND ART

(4-Hydroxyphenoxy)alkane derivatives such as, for example, alkyl 2-(4-hydroxyphenoxy)propionates, are useful intermediates for the synthesis of a wide range of (aryloxyphenoxy)alkane derivatives which have been shown to have herbicidal activity. In the past the required (4-hydroxyphenoxy)alkane derivatives have been prepared either: alkane derivative to give a (4-alkoxyphenoxy)alkane derivative and then cleaving the alkyl residue from the 4-alkoxy group; or derivative.
However, both of these processes suffer the disadvantage advantage of using relatively expensive hydroquinone (derivatives) and the first process suffers the additional disadvantage of requiring the use of relatively expensive reagents to cleave the alkyl residue from the 4-alkoxy group.


DISCLOSURE OF INVENTION

It has now been found that (4-hydroxyphenoxy)alkane derivatives may be prepared from the appropriate phenol obviating the need to use a hydroquinone or a 4-alkoxyphenol.
Accordingly the invention provides a process for the synthesis of a compound of formula I ##STR5## wherein: U and V are independently chosen from the group consisting of hydrogen, halogen, nitro, cyano, thiocyano, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 haloalkenyl, C.sub.1 to C.sub.6 alkoxy, C.sub.1 to C.sub.6 haloalkoxy, C.sub.1 to C.sub.6 alkylthio, carboxy, (C.sub.1 to C.sub.6 alkoxy)carbonyl, phenyl, phenoxy, phenylthio and the groups substituted phenyl, substituted phenoxy and substituted phenylthio wherein in each group the phenyl ring is substituted with from 1 to 3 substituents chosen from the group consisting of halogen, nitro, cyano, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl and C.sub.1 to C.sub.6 alkoxy; alkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkoxyalkyl, C.sub.1 to C.sub.6 haloalkyl, acetyl, propionyl and C.sub.2 to C.sub.6 alkoxycarbonyl, carbonyl, R.sup.2 is chosen from the group consisting of hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkoxyalkyl and C.sub.1 to C.sub.6 haloalkyl, or R.sup.1 and R.sup.2 together may form a methylene, ethylidene, propylidene or isopropylidene group; ##STR6## and CH.sub.2 Z wherein: G is chosen from the group consisting of hydroxy, mercapto, C.sub.1 to C.sub.10 alkoxy, C.sub.1 to C.sub.10 haloalkoxy, C.sub.2 to C.sub.10 alkenyloxy, C.sub.2 to C.sub.10 alkynyloxy, C.sub.1 to C.sub.10 alkylthio, C.sub.2 to C.sub.10 alkenylthio, C.sub.2 to C.sub.10 alkynylthio, C.sub.3 to C.sub.7 cycloalkoxy, C.sub.3 to C.sub.7 cycloalkoxy substituted with 1 or 2 C.sub.1 to C.sub.4 alkyl groups, phenoxy, phenylthio, benzyloxy, benzylthio, the group C.sub.1 to C.sub.10 alkoxy substituted with a substituent chosen from the group consisting of C.sub.1 to C.sub.6 alkoxy, amino, ammonio, cyano, N-(C.sub.1 to C.sub.6 alkyl)amino, N,N-di(C.sub.1 to C.sub.6 alkyl)amino and N,N,N-tri(C.sub.1 to C.sub.6 alkyl)ammonio, the groups phenoxy, phenylthio, benzyloxy and benzylthio wherein in each group the phenyl ring is substituted with from 1 to 3 substituents chosen from the group consisting of halogen, nitro, cyano, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl and C.sub.1 to C.sub.6 alkoxy, the group OM wherein M is the cation of an inorganic or organic base, the group -NHSO.sub.2 R.sup.3 wherein R.sup.3 is chosen from C.sub.1 to C.sub.10 alkyl and C.sub.1 to C.sub.6 haloalkyl, the group --NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently chosen from the group consisting of hydrogen, C.sub.1 to C.sub.6 alkyl, phenyl and benzyl or R.sup.4 and R.sup.5 together form a heterocyclic ring, and the group --O--N=R.sup.6 wherein R.sup.6 is a C.sub.1 to C.sub.10 alkylidene group; Z is chosen from the group consisting of halogen, hydroxy, mercapto, C.sub.1 to C.sub.10 alkoxy, C.sub.1 to C.sub.10 haloalkoxy, C.sub.1

REFERENCES:
patent: 3717669 (1973-02-01), Grant
E. E. Gilbert, "Sulfonation and Related Reactions", (Interscience, New York, 1965), see pp. 379-381, especially p. 380 lines 19 to 22.
"The Merck Index" 9th ed. (Merck, New Jersey 1976), see page ONR-27, Elbs Persulfate Oxidation.
Tetrahedron, vol. 26 (1970), Pergamon Press, pp. 5945 to 5951, Ogata et al., "Kinetics and Orientation in the Peroxy Disulfate Oxidation of Phenol".

Affiliated with

Also associated with

Rating

Process for the synthesis of phenoxyalkane derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the synthesis of phenoxyalkane derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the synthesis of phenoxyalkane derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-41541