Triethylamine → Methyl 2-(benzyloxy)-5-(dimethoxymethyl)benzoate

HRID 1816597Notes

Reaction equation

HRID 1816597 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16](C=O)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]([O:26][CH3:27])([O:24][CH3:25])OC.C(N(CC)CC)C>CO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:21]([O:24][CH3:25])[O:26][CH3:27])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9005Trimethyl orthoformateHCID 22494045Methyl 2-(benzyloxy)-5-formylbenzoate

Product 1

HCID 22494305Methyl 2-(benzyloxy)-5-(dimethoxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

39.1 g of methyl 2-benzyloxy-5-formyl-benzoate was dissolved in 300 ml methanol. 60 ml trimethyl orthoformate and 2 g of p-toluenesulffonic acid were added thereto, followed by heating under reflux for 4 hours. After cooling to room temperature, 5 ml triethylamine was added thereto, and the mixture was evaporated. The residue was dissolved in ethyl acetate, successively washed with water and saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 39.08 g of methyl 2-(benzyloxy)-5-(dimethoxymethyl)benzoate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. customthe mixture was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washsuccessively washed with water and saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d536531e4ee24836b302493058a25f53
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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