Acetone → 4-(2-hydroxyethoxy)-3-methoxybenzaldehyde

HRID 1363481Notes

Reaction equation

HRID 1363481 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][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(O)C>[OH:15][CH2:14][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]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1183VanillinHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 31527124-(2-hydroxyethoxy)-3-methoxybenzaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25.9 g (170 mmol) vanillin (Aldrich), 33.3 g (266 mmol) 2-bromoethanol (Aldrich), 35.2 g (255 mmol) potassium carbonate (Sigma-Aldrich), and 20 g molecular sieves (Aldrich) were combined in a 1 liter round bottom flask equipped with magnetic stirrer and nitrogen inlet. Acetone (600 ml) (Chromasolv for HPLC, >99.9%, Sigma-Aldrich) was added and the reaction mixture was refluxed for 16 hours using an external glycerol heating bath set to 65° C. The solids were filtered and the solvent was removed via rotary evaporation to yield a yellow oil. White crystals were obtained by recrystallization in ethyl alcohol at −20° C. (40% yield).

Workup

  1. customequipped with magnetic stirrer and nitrogen inlet
  2. temperaturethe reaction mixture was refluxed for 16 hours
  3. customset to 65° C
  4. filtrationThe solids were filtered
  5. customthe solvent was removed via rotary evaporation
  6. customto yield a yellow oil

Sources & evidence

ORD record
ord-5af7dc44547d4f008b8395d19d2bdc30
Source dataset
uspto-grants-2011_02
Patent number
US07884228B1

Reaction notes

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