benzyl 2-hydroxy-2-methylpropanoate

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

Procedure: 2-Hydroxyisobutyric acid (15 gm) was dissolved in benzyl alcohol (80 mL) at 0° C. and the solution was saturated with HCl gas. This solution was stored at rt overnight and then was poured into sat. NaHCO3 solution. This was extracted twice with CHCl3 and the combined organic extracts were dried (Na2SO4), filtered and evaporated to dryness. The residue so obtained was fractionally distilled and the title compound was obtained as a fraction that boiled at 85°-100° C. at 0.2 mm. This was extracted twice with CHCl3 the combined organic extracts were dried (Na2SO4) filtered evaporated to dryness The residue so obtained was fractionally distilled

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

Procedure: 2-Hydroxyisobutyric acid (15 gm) was dissolved in benzyl alcohol (80 mL) at 0° C. and the solution was saturated with HCl gas. This solution was stored at rt overnight and then was poured into sat. NaHCO3 solution. This was extracted twice with CHCl3 and the combined organic extracts were dried (Na2SO4), filtered and evaporated to dryness. The residue so obtained was fractionally distilled and the title compound was obtained as a fraction that boiled at 85°-100° C. at 0.2 mm. This was extracted twice with CHCl3 the combined organic extracts were dried (Na2SO4) filtered evaporated to dryness The residue so obtained was fractionally distilled

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

Procedure: To a solution of 2-hydroxy-2-methylpropanoic acid (500 mg, 4.80 mmol) in dry THF (10 ml), NaH (60% dispersion in mineral oil, 192 mg, 4.80 mmol) was added portionwise at 5° C. The resulting mixture was stirred 1 hour at RT. The solvent was removed, the residue was suspended in dry DMF (7 ml), and (bromomethyl)benzene (821 mg, 4.80 mmol) was added followed by a catalytic amount of KI. The reaction was heated under microwave irradiation at 100° C. for 3 hours. After cooling, the solvent was evaporated and the residue was partitioned between water and EtOAc; the organic phase was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (EtOAc/petroleum ether=1/1) affording benzyl 2-hydroxy-2-methylpropanoate as a yellow liquid (773 mg, 3.98 mmol, 83% yield). The solvent was removed The reaction was heated under microwave irradiation at 100° C. for 3 hours After cooling the solvent was evaporated the residue was partitioned between water and EtOAc the organic phase was washed with brine dried over sodium sulfate evaporated to dryness The residue was purified by flash chromatography on silica gel (EtOAc/petroleum ether=1/1)