Dimethylformamide → Methyl 4-ethoxy-3,5-dimethoxybenzoate

HRID 400055Notes

Reaction equation

HRID 400055 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7].CN(C)C=O.[H-].[Na+].I[CH2:24][CH3:25]>C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>[CH3:15][O:14][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:12]=1[O:13][CH2:24][CH3:25])[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70164Methyl Syringate

Product 1

HCID 13652164Methyl 4-ethoxy-3,5-dimethoxybenzoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine methyl 3,5-dimethoxy-4-hydroxy-benzoate (2.12 g, 10 mmol) and dimethylformamide (50 mL). Cool in an ice bath. Add portionwise, sodium hydride (0.4 g, 16.7 mmol). after 2 hours, add iodoethane (4 mL, 50 mmol). Warm to ambient temperature. After 18 hours, dilute the reaction mixture with ethyl acetate and extract with water, 1M hydrochloric acid solution, a saturated sodium bicarbonate solution, and then brine. Dry the organic layer over MgSO4, filtered and evaporated in vacuo to give a residue. chromatograph the residue on silica gel eluting with 5% ethyl acetate/hexane to give methyl 3,5-dimethoxy-4-ethoxy-benzoate.

Workup

  1. temperatureCool in an ice bath
  2. additionAdd portionwise
  3. waitAfter 18 hours
  4. extractionextract with water, 1M hydrochloric acid solution
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-ea702895ec9046fb8d5ba5a2e8342f1b
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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