Preparation of meta-substituted diaryl ethers
AssigneeOccidental Chemical Corporation
InventorsArthur M. Foster, James J. Maul
Life of this patent
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Abstract
A process for the preparation of meta-substituted diaryl ethers comprises reacting an ortho-haloaryl compound with a phenol compound in a non-aqueous medium in the presence of an alkaline metal base. In a specific embodiment m-phenoxytoluene is prepared by reacting orthochlorotoluene with phenol in the presence of an alkaline metal hydroxide in a substantially non-aqueous liquid medium.
Claims23
A process for the preparation of meta-substituted diaryl ethers of the formula ##STR4## wherein R.sub.1 is selected from the group consisting of alkyl and alkoxy of 1 to 30 carbon atoms, aryl and aryloxy of 6 to 14 carbon atoms and 2-(1,3)dioxolyl;
- R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, alkyl and alkoxy of 1 to 30 carbon atoms, aryl and aryloxy of 6 to 14 carbon atoms;
- R.sub.5, R.sub.6, and R.sub.7 are independently selected from the group consisting of hydrogen nitro, alkyl and alkoxy of 1 to 30 carbon atoms, aryl and aryloxy of 6 to 14 carbon atoms;
- R.sub.4 and R.sub.8 are independently selected from the group consisting of hydrogen, nitro, and linear alkyl and alkoxy of 1 to 14 carbon atoms, with the proviso that if either R.sub.4 or R.sub.8 is a substituent of more than 2 carbon atoms the other substituent is hydrogen;
- comprising reacting at atmospheric pressure an ortho-halo aryl compound of the formula ##STR5## wherein R.sub.1, R.sub.2 and R.sub.3 are as previously defined, and halogen is chlorine or bromine;
- with a phenol compound of the formula ##STR6## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as previously defined, and X is hydrogen or an alkali metal;
- in an aprotic, substantially non-nucleophilic, polar solvent at a temperature of about 110.degree. Celsius to about the reflux temperature of the reaction medium, in the presence of an alkali metal base selected from an alkali metal hydroxide and alkali metal carbonate in a molar ratio of alkali metal base:
- phenol compound of greater than about 1.0 to about 4.0 when X is hydrogen and greater than about 0 to about 3.0 when X is an alkali metal.
A process for the preparation of meta-substituted diaryl ethers of the formula ##STR7## wherein R.sub.1 is selected from the group consisting of alkyl and alkoxy of 1 to 30 carbon atoms, aryl and aryloxy of 6 to 14 carbon atoms and 2-(1,3)dioxolyl;
- R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, alkyl and alkoxy of 1 to 30 carbon atoms, aryl and aryloxy of 6 to 14 carbon atoms;
- R.sub.5, R.sub.6, and R.sub.7 are independently selected from the group consisting of hydrogen, nitro, alkyl and alkoxy of 1 to 30 carbon atoms, aryl and aryloxy of 6 to 14 carbon atoms;
- R.sub.4 and R.sub.8 are independently selected from the group consisting of hydrogen, nitro, and linear alkyl and alkoxy of 1 to 14 carbon atoms, with the proviso that if either R.sub.4 or R.sub.8 is a substituent of more than 2 carbon atoms the other substituent is hydrogen;
- comprising reacting at autogenous pressure an ortho-halo aryl compound of the formula ##STR8## wherein R.sub.1, R.sub.2 and R.sub.3 are as previously defined, and halogen is chlorine or bromine;
- with a phenol compound of the formula ##STR9## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as previously defined, and X is hydrogen or an alkali metal;
- at a temperature of from about reflux temperature to about 400.degree. Celsius, in the presence of an alkali metal base selected from an alkali metal hydroxide and an alkali metal carbonate in a molar ratio of alkali metal base:
- phenol compound of greater than about 1.0 to about 4.0 when X is hydrogen and greater than about 0 to about 3.0 when X is an alkali metal.
Dependencies are inferred from the claim text.