Hydrochloric Acid → Ethyl 3-ethoxy-5-hydroxybenzoate

HRID 1295266Notes

Reaction equation

HRID 1295266 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([OH:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].I[CH2:17][CH3:18].Cl>CN(C)C=O.O>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([OH:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl esterHCID 24758Sodium hydride

Product 1

HCID 22930676Ethyl 3-ethoxy-5-hydroxybenzoateYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3,5-dihydroxybenzoate (15.0 g) in N,N-dimethylformamide (180 ml) was gradually added sodium hydride (60% in oil, 3.30 g) at 0° C. and the mixture was stirred for 30 min. Iodoethane (12.9 g) was added and the mixture was further stirred for 2 hrs. The reaction mixture was poured into water, acidified with 2N hydrochloric acid and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and ethyl 3-ethoxy-5-hydroxybenzoate (6.75 g, yield 39%) was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). Recrystallization from diethyl ether-hexane gave colorless needle-shaped crystals. melting point: 62–63° C.

Workup

  1. customat 0° C.
  2. stirringthe mixture was further stirred for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7b5fdb9003e04eb495c7f4010dca50b8
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

Loading…