Vanillin → Ethyl (4-formyl-2-methoxyphenoxy)acetate

HRID 2410093Notes

Reaction equation

HRID 2410093 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])[CH3:18]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 968872Ethyl (4-formyl-2-methoxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A flask containing vanillin (20 g, 0.13 mol), ethyl bromoacetate (28.4 g, 0.17 mol) and potassium carbonate (32.7 g, 0.24 mol) and acetone 200 mL were heated to reflux for 3 hours. The reaction was allowed to come to rt. The acetone was stripped off and the residue partitioned between water and ethyl acetate. The ethyl acetate was washed with brine and dried over magnesium sulfate. The organic layer was concentrated and the solid triturated with hexanes to yield 28.4 grams of example No. 169.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 3 hours
  3. customto come to rt
  4. customthe residue partitioned between water and ethyl acetate
  5. washThe ethyl acetate was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe organic layer was concentrated
  8. customthe solid triturated with hexanes
  9. customto yield 28.4 grams of example No

Sources & evidence

ORD record
ord-746b282f97e74c439316d6202e80a967
Source dataset
uspto-grants-2014_08
Patent number
US08815934B2

Reaction notes

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