Methanol → HCID 12404883, compound

HRID 2359935Notes

Reaction equation

HRID 2359935 reaction equation
[N+:1]([CH:4]([CH3:13])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6])([O-:3])=[O:2].[C:14](OC(=O)C)(=[O:16])[CH3:15].CO>C(OCC)C.CN(C)C1C=CN=CC=1>[C:14]([O:6][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:4]([N+:1]([O-:3])=[O:2])[CH3:13])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 2261182-Nitro-1-phenyl-1-propanol

Product 1

HCID 12404883HCID 12404883, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-nitro-1-phenylpropan-1-ol (32 g) and acetic anhydride (22 mL) in diethyl ether (300 mL) was added 4-dimethylaminopyridine (0.61 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Methanol was added to the reaction mixture, and the mixture was further stirred for 30 min and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 34 g, 86%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70eeaab91e4145e59e7c16da7b57953e
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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