Hydrochloric Acid → 2-(2-Methoxy-6-nitrophenyl)-1-ethanol
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14](=O)[CH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1[O:25][CH3:26])C.Cl>O1CCCC1>[CH3:26][O:25][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:16]=1[CH2:15][CH2:14][OH:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Diisobutylaluminium hydride (20 wt % in toluene; 2.38 g, 16.8 mmol) was added to a solution of (2-methoxy-6-nitro-phenyl)-acetic acid ethyl ester (1.0 g, 4.18 mmol) in tetrahydrofuran (8 mL) at −5° C. The reaction mixture was stirred for 1 h at 0° C. and then poured into 1N hydrochloric acid solution. The mixture was extracted with ethyl acetate (30 mL) then the separated organic phase was washed with water (2×30 mL), brine (25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-(2-methoxy-6-nitro-phenyl)-ethanol (780 mg, 94%).
Workup
- extractionThe mixture was extracted with ethyl acetate (30 mL)
- washthe separated organic phase was washed with water (2×30 mL), brine (25 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a8a3643a7e0a446393130df3c575f707
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524705B2
Reaction notes
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