Benzyl 2-Hydroxy-2-Methylpropionate

In steps 1-4, 2-hydroxy-isobutyric acid was protected with benzyl bromide, alkylated with ethyl iodide, deprotected, and esterified to afford 2-ethoxy-isobutyric acid chloromethyl ester.To a solution of 2-hydroxy-2-methylpropanoic acid (500 mg, 4.80 mmol) in dry THF (10 ml), NaH (60percent 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, 83percent yield).A solution of 2-hydroxy-2-methylpropanoic acid (101, 9.27 g, 89.1 mmol), sodium bicarbonate (7.49 g, 89.1 mmol), benzyl bromide (16.8 g, 98.0 mmol) and tetrabutylammonium iodide (32.9 g, 89.1 mmol) in HTo a solution of 2-hydroxy-2-methylpropanoic acid (500 mg, 4.80 mmol) in dry THF (10 ml), NaH (60percent dispersion in mineral oil, 192 mg, 4.80 mmol) was added portionwise at 5°C. The resulting mixture was stirred lh 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 3h. 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 (EtO Ac/petroleum ether = 1/1) affording benzyl 2-hydroxy-2- methylpropanoate as a yellow liquid (773 mg, 3.98 mmol, 83percent yield).

Molecular Weight:194.23
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:194.094294304
Monoisotopic Mass:194.094294304
Topological Polar Surface Area:46.5
Heavy Atom Count:14
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes