反应详情

温度

10 °C

4'-hydroxy 4-biphenylcarboxylic acid (5.0 g) was added to a stirred suspension of sodium hydride (60% w/w dispersion in mineral oil, 2.34 g) in dry dimethylformamide (45 ml) whilst maintaining the temperature of the reaction mixture below 10° C. The reaction mixture was stirred at 10° C. for 20 minutes. A solution of benzyl bromide (8.4 g) in dry dimethylformamide (10 ml) was added over a period of 10 minutes. The reaction mixture was stirred at 70° C. for 2 hours and the mixture was then poured into cold water (900 ml) to precipitate a solid. The solid was collected by filtration, washed with water (3×200 ml) and added to a mixture of 2M aqueous sodium hydroxide solution (100 ml) and ethanol (100 ml). The mixture was stirred at 100° C. for 12 hours. The ethanol was removed by evaporation and the aqueous residue taken to pH 1.0 by the addition of 12M aqueous hydrochloric acid solution to precipitate a solid. The solid was collected by filtration, washed with water (3×100 ml), ethyl acetate (3×100 ml) and dried to give 4'-benzyloxy-4-biphenylcarboxylic acid (100% yield) as a colourless solid, m.p. >300° C.; m/z 304 (M).

1. temperaturewhilst maintaining the temperature of the reaction mixture below 10° C
2. stirringThe reaction mixture was stirred at 70° C. for 2 hours
3. customto precipitate a solid
4. filtrationThe solid was collected by filtration
5. washwashed with water (3×200 ml)
6. additionadded to a mixture of 2M aqueous sodium hydroxide solution (100 ml) and ethanol (100 ml)
7. stirringThe mixture was stirred at 100° C. for 12 hours
8. customThe ethanol was removed by evaporation
9. additionthe aqueous residue taken to pH 1.0 by the addition of 12M aqueous hydrochloric acid solution
10. customto precipitate a solid
11. filtrationThe solid was collected by filtration
12. washwashed with water (3×100 ml), ethyl acetate (3×100 ml)
13. customdried