Method for the preparation of alkoxyanilines

Claim 1

A method for preparing an o- or p- alkoxyaniline or substituted o- or p- alkoxyaniline which comprises reacting at a temperature of from about 20° to about 250°C. a mixture of a. a nitrobenzene selected from the group consisting of nitrobenzene and substituted nitrobenzene having as an additional substituent on the benzene ring at least one of the following: alkyl of 1 to 4 carbon atoms, halogen and nitro, with the proviso that at least one of the para or ortho positions to the nitro group is unsubstituted; b. an alcohol selected from the group consisting of unsubsituted, branched and unbranched, hydroxyalkyl and hydroxyalkenyl alcohols of 1 to 8 carbon atoms and polyoxyalkylene glycol ether alcohols of the formula: R(OR.sub.1).sub.x OH wherein R is an alkyl of 1 to 4 carbon atoms, R 1 is an ethylene or propylene group and x is 1 to 20; c. a deoxygenating agent selected from the group consisting of phosphorus, sulfur, phosphorus trihalides, sulfur halides in which sulfur has a valence lower than 6, aryl and diaryl phosphorus halides and aryl and diaryl sulfur halides, wherein the aryl group contains 6 to 10 carbon atoms, and triaryl phosphines wherein the aryl group contains 6 to 10 carbon atoms; and d. anhydrous hydrogen fluoride, said mixture containing a molar ratio of from about 1:1 to about 50:1 of said alcohol to said selected nitrobenzene, a molar ratio of from about 0.3:1 to about 5:1 of said deoxygenating agent to said selected nitrobenzene and a molar ratio of about 1:1 to about 50:1 of said hydrogen fluoride to said selected nitrobenzene and then separating said resulting o- or p- alkoxyaniline or o- or p- substituted alkoxyaniline from the reaction mixture.

Claim 2

A method for preparing an o- or p- alkoxyaniline or substituted o- or p- alkoxyaniline which comprises reacting at a temperature of from about 20° to about 250°C. a mixture of a. a nitrobenzene selected from the group consisting of nitrobenzene and substituted nitrobenzene having as an additional substituent on the benzene ring at least one of the following: alkyl of 1 to 4 carbon atoms, halogen and nitro, with the proviso that at least one of the para or ortho positions to the nitro group is unsubstituted; b. an alcohol selected from the group consisting of unsubsituted, branched and unbranched, hydroxyalkyl and hydroxyalkenyl alcohols of 1 to 8 carbon atoms and polyoxyalkylene glycol ether alcohols of the formula: R(OR.sub.1).sub.x OH wherein R is an alkyl of 1 to 4 carbon atoms, R 1 is an ethylene or propylene group and x is 1 to 20; c. a deoxygenating agent selected from the group consisting of phosphorus, sulfur, phosphorus trihalides, sulfur halides in which sulfur has a valence lower than 6, aryl and diaryl phosphorus halides and aryl and diaryl sulfur halides, wherein the aryl group contains 6 to 10 carbon atoms, and triaryl phosphines wherein the aryl group contains 6 to 10 carbon atoms; and d. anhydrous hydrogen fluoride, said mixture containing a molar ratio of from about 1:1 to about 50:1 of said alcohol to said selected nitrobenzene, a molar ratio of from about 0.3:1 to about 5:1 of said deoxygenating agent to said selected nitrobenzene and a molar ratio of about 1:1 to about 50:1 of said hydrogen fluoride to said selected nitrobenzene and then separating said resulting o- or p- alkoxyaniline or o- or p- substituted alkoxyaniline from the reaction mixture.