Ethanol → Ethyl 2-methoxy-6-nitrophenylacetate

HRID 37869

Reaction equation

HRID 37869 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:9]=1[CH2:17][C:18]#N.[CH2:20]([OH:22])[CH3:21]>>[CH2:20]([O:22][C:18](=[O:2])[CH2:17][C:9]1[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH3:6])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5550182-(2-Methoxy-6-nitrophenyl)acetonitrile

Product 1

HCID 58216762Ethyl 2-methoxy-6-nitrophenylacetateYield 72%

Procedure

Sulfuric acid (1 mL) was slowly added to a solution of (2-methoxy-6-nitro-phenyl)-acetonitrile (200 mg, 1.04 mmol) in 95% ethanol (2 mL). The mixture was heated at reflux overnight then quenched into ice cold water and extracted with diethyl ether (10 mL). The organic phase was washed with water (2×10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford (2-methoxy-6-nitro-phenyl)-acetic acid ethyl ester (180 mg, 72%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customthen quenched into ice cold water
  4. extractionextracted with diethyl ether (10 mL)
  5. washThe organic phase was washed with water (2×10 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-202240da0fa5439b9bc95d88814baa97
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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