Hydrochloric Acid → 2-(2-Methoxy-6-nitrophenyl)-1-ethanol

HRID 880480Notes

Reaction equation

HRID 880480 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:14]=1[CH2:22][C:23]([O-])=[O:24].Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:14]=1[CH2:22][CH2:23][OH:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 26338608HCID 26338608, compound

Product 1

HCID 227203652-(2-Methoxy-6-nitrophenyl)-1-ethanolYield 94.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminium hydride (20 wt %; 2.38 g, 16.8 mmol) in toluene was added to a solution of 2-(2-methoxy-6-nitro-phenyl)acetate (1.0 g, 4.18 mmol) in tetrahydrofuran (8 mL) at −5° C. The reaction mixture was stirred at 0° C. for 1 h and then poured into 1N hydrochloric acid. The mixture was extracted with ethyl acetate (30 mL) and 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

  1. extractionThe mixture was extracted with ethyl acetate (30 mL)
  2. washthe separated organic phase was washed with water (2×30 mL), brine (25 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95b020f04c5742c7a3b469e51174a60c
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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