Ethyl Bromide → Ethyl 4-ethoxy-3-hydroxybenzoate

HRID 967429Notes

Reaction equation

HRID 967429 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH3:21]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][CH3:21])=[C:7]([OH:12])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 77547Ethyl 3,4-Dihydroxybenzoate

Product 1

HCID 11106619Ethyl 4-ethoxy-3-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

5 g (27.2 mmol) of 3,4-Dihydroxy-benzoic acid ethyl ester was dissolved in 100 ml DMF and 3.75 g (27.2 mmol) of potassium carbonate was added. The solution was cooled to 0° C. and a solution of 2.96 g (27.2 mmol) ethyl bromide in 10 ml DMF was added dropwise. The solution was stirred for 16 h at room temperature (RT). The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/4).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe solution was washed three times with water
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/4)

Sources & evidence

ORD record
ord-56d4435aa8704547966a5f44b290f016
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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