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

HRID 1375076Notes

Reaction equation

HRID 1375076 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>[CH2:15]([O:13][C:12](=[O:14])[CH2:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([OH:1])[CH:3]=1)[CH3:16]

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-nitro-phenyl)-acetic 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 methyl ether 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 methyl ether
  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-7eed91bfa1ed400d9e08681fc63f30d2
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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