Vanillin → Veratraldehyde

HRID 1262706Notes

Reaction equation

HRID 1262706 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.[C:12](=O)([O-])[O-].[K+].[K+].P(OC)(OC)(OC)=O>>[CH:2](=[O:1])[C:3]1[CH:11]=[CH:10][C:8]([O:9][CH3:12])=[C:5]([O:6][CH3:7])[CH:4]=1

Participants

4

Reactant 3

HCID 1183VanillinHCID 10541Trimethyl PhosphateHCID 11430Potassium Carbonate

Product 1

HCID 8419VeratraldehydeYield 111.2%

Conditions

Temperature
35 °C

Procedure

In an apparatus similar to Example 1, 15.0 g (0.099 mol) of vanillin and 10.0 g (0.072 mol) of anhydrous potassium carbonate were heated under nitrogen to 90° C. To this clear slurry was added over about 10 minutes 13.5 ml (0.112 mol) of trimethyl phosphate while holding the temperature below 110° C. The mixture was stirred and heated to 65°-75° C. for three hours then cooled to 35° C. and quenched with 80 ml of water to precipitate an oil. On stirring a light powder precipitated which was filtered, washed with three 100 ml portions of water, and dried to give 13.3 g (81%) of veratraldehyde.

Workup

  1. customthe temperature below 110° C
  2. temperatureheated to 65°-75° C. for three hours
  3. customquenched with 80 ml of water
  4. customto precipitate an oil
  5. stirringOn stirring a light powder
  6. customprecipitated which
  7. filtrationwas filtered
  8. washwashed with three 100 ml portions of water
  9. customdried

Sources & evidence

ORD record
ord-6c25d32901024520b8cd542ea1d58661
Source dataset
uspto-grants-1984_06
Patent number
US04453004

Reaction notes

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