3,4,5-Trimethoxybenzaldehyde → 3,4,5-Trimethoxybenzaldehyde dimethyl acetal

HRID 974108Notes

Reaction equation

HRID 974108 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])C=O.CO[CH:17]([O:20][CH3:21])[O:18][CH3:19].C[O-].[Na+]>CO.Cl>[CH3:21][O:20][CH:17]([O:18][CH3:19])[C:5]1[CH:8]=[C:9]([O:13][CH3:14])[C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 9005Trimethyl orthoformateHCID 10942334Sodium Methoxide

Product 1

HCID 41935783,4,5-Trimethoxybenzaldehyde dimethyl acetalYield 100.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 196.2 g of 3,4,5-trimethoxybenzaldehyde, 127.3 g of trimethoxymethane, 200 ml of methanol and 0.1 g of hydrochloric acid is refluxed for 3 hours. After cooling the reaction mixture, 0.2 g of a 24% sodium methoxide solution in methanol is added thereto and the mixture is evaporated under reduced pressure to remove solvent. 150 ml of tetrahydrofuran are added to the residue, and the mixture is evaporated under reduced pressure to remove solvent. 243 g of 3,4,5-trimethoxybenzaldehyde dimethyl acetal are thereby obtained as a pale yellow oil.

Workup

  1. temperatureis refluxed for 3 hours
  2. additionis added
  3. customthe mixture is evaporated under reduced pressure
  4. customto remove solvent
  5. addition150 ml of tetrahydrofuran are added to the residue
  6. customthe mixture is evaporated under reduced pressure
  7. customto remove solvent

Sources & evidence

ORD record
ord-eac34bc471ee4134868a9133acfe0832
Source dataset
uspto-grants-1991_11
Patent number
US05066825

Reaction notes

Loading…