2-butan-2-yloxyacetic acid

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

Procedure: To a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer, reflux condenser and addition funnel was added 500 ml of 2-butanol under nitrogen. Sodium spheres (3.31 g, 0.144 moles) were then added and the mixture heated at reflux for 6 hours and then stirred at room temperature overnight. A solution of bromoacetic acid (10.00 g, 0.072 moles) in 10 ml of 2-butanol was then added dropwise and the mixture stirred at room temperature for 24 hours. The mixture was then concentrated in vacuo to remove the 2-butanol and the resulting white solid dissolved in 100 ml of water. This aqueous solution was washed with ether (2×50 ml) and then acidified to pH 1 with concentrated hydrochloric acid. The resulting mixture was extracted with ether (3×100 ml) and the combined extracts washed with saturated sodium chloride solution (1×50 ml), dried over magnesium sulfate and concentrated in vacuo to give 8.1 g of the product as a pale yellow oil. To a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer reflux condenser and addition funnel were then added the mixture heated at reflux for 6 hours the mixture stirred at room temperature for 24 hours The mixture was then concentrated in vacuo to remove the 2-butanol the resulting white solid dissolved in 100 ml of water This aqueous solution was washed with ether (2×50 ml) The resulting mixture was extracted with ether (3×100 ml) the combined extracts washed with saturated sodium chloride solution (1×50 ml) dried over magnesium sulfate concentrated in vacuo

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

Procedure: To a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer, reflux condenser and addition funnel was added 500 ml of 2-butanol under nitrogen. Sodium spheres (3.31 g, 0.144 moles) were then added and the mixture heated at reflux for 6 hours and then stirred at room temperature overnight. A solution of bromoacetic acid (10.00 g, 0.072 moles) in 10 ml of 2-butanol was then added dropwise and the mixture stirred at room temperature for 24 hours. The mixture was then concentrated in vacuo to remove the 2-butanol and the resulting white solid dissolved in 100 ml of water. This aqueous solution was washed with ether (2×50 ml) and then acidified to pH 1 with concentrated hydrochloric acid. The resulting mixture was extracted with ether (3×100 ml) and the combined extracts washed with saturated sodium chloride solution (1×50 ml), dried over magnesium sulfate and concentrated in vacuo to give 8.1 g of the product as a pale yellow oil. To a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer reflux condenser and addition funnel were then added the mixture heated at reflux for 6 hours the mixture stirred at room temperature for 24 hours The mixture was then concentrated in vacuo to remove the 2-butanol the resulting white solid dissolved in 100 ml of water This aqueous solution was washed with ether (2×50 ml) The resulting mixture was extracted with ether (3×100 ml) the combined extracts washed with saturated sodium chloride solution (1×50 ml) dried over magnesium sulfate concentrated in vacuo

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

Procedure: To a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer, reflux condenser and addition funnel was added 500 ml of 2-butanol under nitrogen. Sodium spheres (3.31 g, 0.144 moles) were then added and the mixture heated at reflux for 6 hours and then stirred at room temperature overnight. A solution of bromoacetic acid (10.00 g, 0.072 moles) in 10 ml of 2-butanol was then added dropwise and the mixture stirred at room temperature for 24 hours. The mixture was then concentrated in vacuo to remove the 2-butanol and the resulting white solid dissolved in 100 ml of water. This aqueous solution was washed with ether (2×50 ml) and then acidified to pH 1 with concentrated hydrochloric acid. The resulting mixture was extracted with ether (3×100 ml) and the combined extracts washed with saturated sodium chloride solution (1×50 ml), dried over magnesium sulfate and concentrated in vacuo to give 8.1 g of the product as a pale yellow oil. To a 3-neck 1-liter round-bottom flask equipped with a mechanical stirrer reflux condenser and addition funnel were then added the mixture heated at reflux for 6 hours the mixture stirred at room temperature for 24 hours The mixture was then concentrated in vacuo to remove the 2-butanol the resulting white solid dissolved in 100 ml of water This aqueous solution was washed with ether (2×50 ml) The resulting mixture was extracted with ether (3×100 ml) the combined extracts washed with saturated sodium chloride solution (1×50 ml) dried over magnesium sulfate concentrated in vacuo