Iodoethane → Ethyl 4-ethoxy-3-hydroxybenzoate

HRID 521438Notes

Reaction equation

HRID 521438 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+].I[CH2:21][CH3:22]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:21][CH3:22])=[C:7]([OH:12])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium Carbonate2×HCID 77547Ethyl 3,4-Dihydroxybenzoate

Product 1

HCID 11106619Ethyl 4-ethoxy-3-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dihydroxybenzoic acid ethyl ester (3.00 g, 16.0 mmol) was suspended in DMF (10 ml), potassium carbonate (2.21 g, 16.0 mmol) was added, the mixture was stirred for 5 min at room temperature, and then iodoethane (2.49 g, 16.0 mmol) was added. The mixture was stirred overnight, the addition of potassium carbonate and of iodoethane was repeated, and the mixture was stirred overnight again. The mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase extracted with EA, and the combined organic extracts were washed with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient).

Workup

  1. stirringThe mixture was stirred overnight
  2. stirringthe mixture was stirred overnight again
  3. customThe mixture was partitioned between 2 N hydrochloric acid and EA
  4. extractionthe aqueous phase extracted with EA
  5. washthe combined organic extracts were washed with a saturated sodium hydrogencarbonate solution
  6. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-04fe2bd3fdd241608a368826546293b5
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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