Hydrochloric Acid → 4-Ethyl-2-nitrophenol

HRID 1723000Notes

Reaction equation

HRID 1723000 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:7].Cl>O.CCOCC>[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:1]([O-:4])=[O:2])[CH:9]=1)[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24268Sodium NitrateHCID 312424-Ethylphenol

Product 1

HCID 919014-Ethyl-2-nitrophenolYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 130 ml of water, 130 ml of ether, 7.66 g of sodium nitrate and 10.0 g of 4-ethylphenol was added 13 ml of concentrated hydrochloric acid, and the reaction was continued at room temperature for 3 days. To the reaction mixture was added 300 ml of water and the mixture was extracted with 500 ml of ether. The extract was washed with water, then a brine and dried with anhydrous sodium sulfate. The drying agent was filtered off and the solvent was distilled away under reduced pressure to give 13.0 g of 4-ethyl-2-nitrophenol.

Workup

  1. extractionthe mixture was extracted with 500 ml of ether
  2. washThe extract was washed with water
  3. dry with materiala brine and dried with anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-492c0ad2a3a2471587912d753b32257c
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

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