Hydrochloric Acid → Ethyl (3-nitrophenyl)acetate

HRID 1858237Notes

Reaction equation

HRID 1858237 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH2:15](O)[CH3:16]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:15][CH3:16])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 158763-Nitrophenylacetic acid

Product 1

HCID 14997011Ethyl (3-nitrophenyl)acetateYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 g (60 mmol) of 3-nitrophenylacetic acid in 120 ml of ethanol were added 20 ml of a saturated solution of hydrogen chloride in ethyl acetate and the mixture was heated at reflux for 4 hours, cooled and left to stand at room temperature for 18 hours. The mixture was evaporated and the residue was partitioned between 120 ml of diethyl ether and 100 ml of saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 10.3 g (82%) of ethyl 3-nitrophenylacetate as a pale yellow oil. [NMR spectrum (250 MHz) δ1.25(t) (3H), δ3.68(s) (2H), δ4.6(q) (2H), δ6.5-δ6.7(m) (3H), δ7.09(dd) (1H)].

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. waitleft
  5. customThe mixture was evaporated
  6. customthe residue was partitioned between 120 ml of diethyl ether and 100 ml of saturated aqueous sodium bicarbonate solution
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-1bd671cd37144098a707cf1564aebd42
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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