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Dolbier HW Solutions 548

Dolbier HW Solutions 548 - 642 AMINES(e Conversion of...

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Unformatted text preview: 642 AMINES (e) Conversion of o-fluoroanisole to 4-amino-2-fluoroanisole proceeds in the conventional way by preparation and reduction of a nitro derivative. Once the necessary arylamine is at hand, it is converted to the nitrile by a Sandmeyer reaction. Diazotization followed by hydrolysis of the 4-amino-2-fluoroanisole prepared as an intermediate in part (d ) yields the desired phenol. OCH3 OCH3 NH2 OCH3 F F 1. NaNO2, H2SO4, H2O as in part (d ) 2. heat NH2 o-Anisidine 22.41 (a) OH 4-Amino-2fluoroanisole 3-Fluoro-4methoxyphenol (70%) The carboxyl group of p-aminobenzoic acid can be derived from the methyl group of p-methylaniline by oxidation. First, however, the nitrogen must be acylated so as to protect the ring from oxidation. CO2H CO2H CH3 NH2 NHCCH3 NH2 O p-Aminobenzoic acid p-Methylaniline The sequence of reactions to be used is CH3 CH3 OO CH3COCCH3 CO2H CO2H K2Cr2O7, H2SO4 NH2 1. HCl, H2O H2O, heat 2. neutralize HNCCH3 O (b) O p -Methylacetanilide p -Methylaniline HNCCH3 p -Acetamidobenzoic acid O F Main Menu NH2 CCH2CH3 Ethyl p -fluorophenyl ketone Forward p -Aminobenzoic acid Attachment of fluoro and propanoyl groups to a benzene ring is required. The fluorine substituent can be introduced by way of the diazonium tetrafluoroborate, the propanoyl group by way of a Friedel– Crafts acylation. Because the fluorine substituent is ortho, para-directing, introducing it first gives the proper orientation of substituents. F Back NH2 TOC Fluorobenzene Study Guide TOC Aniline Student OLC MHHE Website ...
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