Ethanol → Ethyl 2-methoxy-6-nitrophenylacetate

HRID 880479

Reaction equation

HRID 880479 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]>>[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]([O:22][CH2:20][CH3:21])=[O:2]

Participants

4

Reactant 3

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

Product 1

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

Procedure

Concentrated sulfuric acid (1 mL) was slowly added to a solution of 2-(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 ethyl 2-(2-methoxy-6-nitro-phenyl)acetate (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-15401094f43248089cabd82a2e11e9e2
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Linked notes

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