Syringaldehyde → 3,4,5-Trimethoxybenzaldehyde

HRID 1262729Notes

Reaction equation

HRID 1262729 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].P(OC)(OC)(OC)=O>>[CH3:11][O:10][C:9]1[CH:12]=[C:2]([CH:3]=[C:4]([O:5][CH3:6])[C:7]=1[O:8][CH3:14])[CH:1]=[O:13]

Participants

4

Reactant 3

HCID 8655SyringaldehydeHCID 10541Trimethyl PhosphateHCID 11430Potassium Carbonate

Product 1

HCID 68583,4,5-TrimethoxybenzaldehydeYield 92.1%

Conditions

Temperature
80 °C

Procedure

In an apparatus similar to Example 1, 15.2 g (0.083 mol) of syringaldehyde and 15.0 g (0.11 mol) of potassium carbonate were heated to 105° C. under nitrogen and 15 ml (0.12 mol) of trimethyl phosphate were added over 10 minutes. The mixture was maintained at about 80° C. for 3 hours then cooled to 45° C. and quenched with 50 ml of H2O. The tan solid which precipitated was collected, washed with 3×50 ml of water and dried to give 15 g (92%) of 3, 4, 5-trimethoxybenzaldehyde.

Workup

  1. temperaturethen cooled to 45° C.
  2. customquenched with 50 ml of H2O
  3. customThe tan solid which precipitated
  4. customwas collected
  5. washwashed with 3×50 ml of water
  6. customdried

Sources & evidence

ORD record
ord-d12ee9eacb554ae99a93498a80623cdb
Source dataset
uspto-grants-1984_06
Patent number
US04453017

Reaction notes

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