Ethanol → Ethyl 2-(3-hydroxy-4-nitrophenyl)acetate

HRID 49703Notes

Reaction equation

HRID 49703 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:15](O)[CH3:16]>Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 702EthanolHCID 235083252-(3-Hydroxy-4-nitrophenyl)acetic acid

Product 1

HCID 23508320Ethyl 2-(3-hydroxy-4-nitrophenyl)acetate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A solution of 3-hydroxy-4-nitrophenylacetic acid (4.0 g, prepared according to the procedure described by Meyer et al, J.Med.Chem., 1997, 40, pages 1049-1062) in ethanol (approximately 100 mL) was treated with concentrated hydrochloric acid (5-8 drops) was heated at reflux temperature for 3 hours then evaporated. The residue was dissolved in tert-butyl methylether and the solution was washed with saturated aqueous sodium bicarbonate solution, then with water, then dried, and then evaporated to give the title compound (5.0 g) as a light yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 hours
  3. customthen evaporated
  4. dissolutionThe residue was dissolved in tert-butyl methylether
  5. washthe solution was washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialwith water, then dried
  7. customevaporated

Sources & evidence

ORD record
ord-d308b8da7bb94c82a8950bd040312d69
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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