Reaction #607401

Reaction equation

2-amino-2-(4-chloro-3-methylphenyl)acetic acid

lithium aluminum hydride

→

title compound

Yield 101.4%

2-amino-2-(4-chloro-3-methylphenyl)ethanol

Yield 101.4%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe reaction was refluxed for 18 hours
2. 2
   TemperatureThe reaction was cooled
3. 3
   Otherquenched with ice water
4. 4
   ExtractionThe reaction was extracted with ethyl acetate
5. 5
   Washwashed with water, and brine
6. 6
   DryingThe combined organic layers were dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

To 2-amino-2-(4-chloro-3-methylphenyl)acetic acid (1.7 g, 8.5 mmol) in tetrahydrofuran (0.4 M) at 0° C. was added lithium aluminum hydride (2 M, 8.5 mL, 17 mmol) dropwise. The reaction was refluxed for 18 hours. The reaction was cooled and quenched with ice water. The reaction was extracted with ethyl acetate, washed with water, and brine. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to provide the title compound as a yellow solid (1.6 g, quantitative): 1H NMR (300 MHz, DMSO-d6) δ 7.44-7.23 (m, 2H), 7.18 (dd, J=8.2, 2.2 Hz, 1H), 4.77 (bs, 2H), 3.81 (dd, J=7.8, 4.8 Hz, 1H), 3.53-3.14 (m, 3H), 2.30 (s, 3H); ESIMS m/z 186 ([M+H]+).

Source