反应详情

A solution of 2.20 g (0.0098 mole) of methyl 2-(2-hydroxymethyl-5-methylphenoxy)propionate in 10 mL of dry methylene chloride was added to a colorless solution of 1.28 g (0.0108 mole) of thionyl chloride and 5 drops of pyridine in 10 mL of dry methylene chloride during a 10 minute period. This mixture was heated at reflux for one hour and then poured into 50 mL of water. The phases were separated, and the aqueous phase was extracted three times with methylene chloride. These extracts were combined with the organic phase, which was then washed three times with a saturated aqueous solution of sodium bicarbonate and once with a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure, leaving a yellow oil as a residue. This oil was placed on a silica gel column and eluted with methylene chloride. After the product-containing fractions were combined and the solvent evaporated under reduced pressure, 2.06 g of methyl 2-(2-chloromethyl-5-methylphenoxy)propionate was recovered as a colorless oil. The NMR spectrum was consistent with the proposed structure.

1. temperatureThis mixture was heated
2. temperatureat reflux for one hour
3. customThe phases were separated
4. extractionthe aqueous phase was extracted three times with methylene chloride
5. washwas then washed three times with a saturated aqueous solution of sodium bicarbonate
6. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customthe filtrate was evaporated under reduced pressure
9. customleaving a yellow oil as a residue
10. washeluted with methylene chloride
11. customthe solvent evaporated under reduced pressure, 2.06 g of methyl 2-(2-chloromethyl-5-methylphenoxy)propionate
12. customwas recovered as a colorless oil