Nitric Acid → 4-Hydroxy-3-nitrophenethyl chloride

HRID 484328Notes

Reaction equation

HRID 484328 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][Cl:12])=[CH:8][CH:7]=1.O>C(O)(=O)C>[OH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][Cl:12])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 3167214-(2-Chloroethyl)phenol

Product 1

HCID 194383584-Hydroxy-3-nitrophenethyl chlorideYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of concentrated nitric acid (1.8 ml) in acetic acid (4 ml) was added to a stirred solution of 4-hydroxyphenethyl chloride (4.5 g) in acetic acid (25 ml), keeping the temperature below 15°. The mixture was then stirred at 10° for 3.5 hours, poured into water, and extracted into ethyl acetate. The organic extract was washed with 5% aqueous sodium carbonate solution, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (50 g) using hexane plus 0-10% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless solid (3.2 g, 55%), m.p. 53°-55°.

Workup

  1. customthe temperature below 15°
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with 5% aqueous sodium carbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica (50 g)
  8. customevaporated

Sources & evidence

ORD record
ord-8977f89b59f44d638bb806231c536c59
Source dataset
uspto-grants-1993_07
Patent number
US05231104

Reaction notes

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