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

HRID 1296205Notes

Reaction equation

HRID 1296205 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8](C=O)[CH:7]=[CH:6][C:5]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:21]([O:26][CH3:27])([O:24][CH3:25])OC.C(N(CC)CC)C>CO>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:21]([O:24][CH3:25])[O:26][CH3:27])[CH:7]=[CH:6][C:5]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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 2-benzyloxy-5-formylbenzoic acid methyl ester was dissolved in 300 ml of methanol. 60 ml of trimethyl orthoformate and 2 g of p-tosylic acid were added thereto, and the solution was heated under refluxed for 4 hours. After the solution was cooled down to room temperature, 5 ml of triethylamine was added thereto, and the solution was evaporated. The residue was dissolved in ethyl acetate, and the solution was successively washed with water and saturated sodium bicarbonate water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 39.08 g of 2-(benzyloxy)-5-(dimethoxymethyl)benzoic acid methyl ester.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder refluxed for 4 hours
  3. customthe solution was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was successively washed with water and saturated sodium bicarbonate water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7501740c4d8044849f638aaaa096dbfb
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Reaction notes

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