Vanillin → Veratraldehyde

HRID 462137Notes

Reaction equation

HRID 462137 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.S(OC)(O[CH3:16])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH:2](=[O:1])[C:3]1[CH:11]=[CH:10][C:8]([O:9][CH3:16])=[C:5]([O:6][CH3:7])[CH:4]=1

Participants

5

Reactant 3

HCID 1183VanillinHCID 6497Dimethyl SulfateHCID 10340Sodium Carbonate

Product 1

HCID 8419Veratraldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

100 g of vanillin (0.658 mol), 128 g of dimethyl sulfate (1.00 mol), and 96.0 g of sodium carbonate (0.91 mol) were heated with stirring to 80° C over b 0.5 hr. Stirring was continued at this temperature for 1.0 hr. over which time 60 ml of water were added in 5 ml portions. Work-up as in Example 1 gave a quantitative yield of veratraldehyde which contained not more than 0.1% vanillin, as determined by g.l.c. analysis.

Workup

  1. stirringStirring
  2. waitwas continued at this temperature for 1.0 hr

Sources & evidence

ORD record
ord-cc31fdcb3ae5429a85820267984c2e86
Source dataset
uspto-grants-1977_12
Patent number
US04065504

Reaction notes

Loading…