Vanillin → 3-Methoxy-4-(methoxymethoxy)benzaldehyde

HRID 2254206Notes

Reaction equation

HRID 2254206 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20]Cl>C(C1C=CC=CC=1)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:11][CH2:18][O:19][CH3:20])[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 796613-Methoxy-4-(methoxymethoxy)benzaldehydeYield 53.1%

Reagents, catalysts & solvents 1

HCID 7410AcetophenoneSolvent

Procedure

To 14.0 g of vaniline and 51.0 g of potassium carbonate was added 280 ml of acetophenone, and chloromethyl methyl ether was further added and the mixture was refluxed for 1 hour. The reaction liquid was cooled to room temperature and filtered, and the filtrate was concentrated under reduced pressure. The reaction mixture was dissolved in ether, washed with water, shaken with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to the column chromatography [230-400 mesh Kieselgel; eluting solvent=hexane/ethyl acetate (2/1)] to obtain 9.6 g (yield=53.1%) of 3-methoxy-4methoxymethoxybenzaldehyde.

Workup

  1. additionwas further added
  2. temperaturethe mixture was refluxed for 1 hour
  3. customThe reaction liquid
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe reaction mixture was dissolved in ether
  7. washwashed with water
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e055e10ff53b488c89109b6ce53e73fb
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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