methyl 2-[4-(2-methylpropyl)phenyl]acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.05 g of sodium and 8 ml of 3-hydroxymethylpyridine was heated at 65°-70° C. for 10 hours. To this mixture was added 2.1 g of p-isobutylphenylacetic acid methyl ester, and the whole was heated at 95°-100° C. for 8 hours. After the reaction was complete, 100 ml of water was added. The resulting mixture was extracted with ether, and the ether layer separated was dehydrated and concentrated to leave an oily residue. This residue was distilled under reduced pressure to give 1.9 g of p-isobutylphenylacetic acid-3-pyridylmethyl ester as a colorless liquid, boiling at 142°-145° C./1 mmHg. Analysis-Calculated for C18H21NO2 : C, 76.29; H, 7.47; N, 4.94. Found: C, 76.02; H, 7.38; N, 4.79. Mass spectrum: parent ion 283 m/e. was heated at 65°-70° C. for 10 hours the whole was heated at 95°-100° C. for 8 hours The resulting mixture was extracted with ether the ether layer separated concentrated to leave an oily residue This residue was distilled under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.05 g of sodium and 8 ml of 3-hydroxymethylpyridine was heated at 65°-70° C. for 10 hours. To this mixture was added 2.1 g of p-isobutylphenylacetic acid methyl ester, and the whole was heated at 95°-100° C. for 8 hours. After the reaction was complete, 100 ml of water was added. The resulting mixture was extracted with ether, and the ether layer separated was dehydrated and concentrated to leave an oily residue. This residue was distilled under reduced pressure to give 1.9 g of p-isobutylphenylacetic acid-3-pyridylmethyl ester as a colorless liquid, boiling at 142°-145° C./1 mmHg. Analysis-Calculated for C18H21NO2 : C, 76.29; H, 7.47; N, 4.94. Found: C, 76.02; H, 7.38; N, 4.79. Mass spectrum: parent ion 283 m/e. was heated at 65°-70° C. for 10 hours the whole was heated at 95°-100° C. for 8 hours The resulting mixture was extracted with ether the ether layer separated concentrated to leave an oily residue This residue was distilled under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.05 g of sodium and 8 ml of 3-hydroxymethylpyridine was heated at 65°-70° C. for 10 hours. To this mixture was added 2.1 g of p-isobutylphenylacetic acid methyl ester, and the whole was heated at 95°-100° C. for 8 hours. After the reaction was complete, 100 ml of water was added. The resulting mixture was extracted with ether, and the ether layer separated was dehydrated and concentrated to leave an oily residue. This residue was distilled under reduced pressure to give 1.9 g of p-isobutylphenylacetic acid-3-pyridylmethyl ester as a colorless liquid, boiling at 142°-145° C./1 mmHg. Analysis-Calculated for C18H21NO2 : C, 76.29; H, 7.47; N, 4.94. Found: C, 76.02; H, 7.38; N, 4.79. Mass spectrum: parent ion 283 m/e. was heated at 65°-70° C. for 10 hours the whole was heated at 95°-100° C. for 8 hours The resulting mixture was extracted with ether the ether layer separated concentrated to leave an oily residue This residue was distilled under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure of example 1, a mixture of 2 g of methyl (4-isobutylphenyl)acetate (EP 347,939), 16 ml of dimethyl carbonate and 2 g of K2CO3, in a 1:20:1.5 molar ratio, is reacted in autoclave at a temperature of 210° C. The reaction is completed within about 8 hours. The product, methyl α-(4-isobutylphenyl)propionate, is hydrolyzed to α-(4-isobutyl)propionic acid (Ibuprofen) as in the examples above. Yield (starting from the not methylated ester): 90%. in a 1:20:1.5 molar ratio, is reacted in autoclave at a temperature of 210° C Yield (