Ethylvanillin → 2-(2-Ethoxy-4-formylphenoxy)acetic acid

HRID 1598809Notes

Reaction equation

HRID 1598809 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23]C(C)(C)C)=[O:22]>CN(C=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:20][C:21]([OH:23])=[O:22])=[C:3]([O:10][CH2:11][CH3:12])[CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 8467EthylvanillinHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 8015372-(2-Ethoxy-4-formylphenoxy)acetic acidYield 120.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-3-ethoxybenzaldehyde (5.0 g, 36 mmol), potassium carbonate (5.0 g, 36 mmol), and t-butyl bromoacetate (5.9 mL, 36 mmol) were heated to 55° C. overnight in DMF (35 mL). After removal of solvent, the mixture was extracted with EtOAc and water, then brine. After drying (Na2SO4), solvent was removed no yield a white solid (9.7 g). mp 90°-92.6° C. MS(NH3): 298 (base, M+NH4).

Workup

  1. customAfter removal of solvent
  2. extractionthe mixture was extracted with EtOAc and water
  3. dry with materialAfter drying (Na2SO4), solvent
  4. customwas removed

Sources & evidence

ORD record
ord-f35afbec73174a538b72b0957760d918
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

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