Methanol → 3-Nitrophenylethyl alcohol

HRID 1256153Notes

Reaction equation

HRID 1256153 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11](OC)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CO.O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 526967Methyl 2-(3-nitrophenyl)acetate

Product 1

HCID 1040583-Nitrophenylethyl alcoholYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(3-nitrophenyl)acetate (12 g, 62 mmol) in THF (100 ml) was cooled to 0° C., then MeOH (10 mL) was added slowly, followed by stirring at room temperature overnight. Water was added to terminate the reaction. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 2-(3-nitrophenyl)ethanol (9 g, yield 90%). 1H NMR: 400 MHz CDCl3 δ 8.11-8.07 (m, 2H), 7.59-7.56 (m, 1H), 7.49-7.45 (m, 1H), 3.94-3.91 (m, 2H), 2.99-2.96 (m, 2H).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-68316caa138e488d90f9ec96455fcb9f
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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