Trimethyl orthoformate → Benzoic acid, 4-(dimethoxymethyl)-, methyl ester

HRID 1025915Notes

Reaction equation

HRID 1025915 reaction equation
C([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH:13]([O:18][CH3:19])([O:16][CH3:17])OC>CO.S(=O)(=O)(O)O.C(Cl)Cl>[CH3:19][O:18][CH:13]([O:16][CH3:17])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 9005Trimethyl orthoformateHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 170620Benzoic acid, 4-(dimethoxymethyl)-, methyl esterYield 102.5%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-formylbenzoate (CAS [1571-08-0] 5.33 g, 32.5 mmol) in methanol (40 mL) were added trimethyl orthoformate (7.5 mL, 68.25 mmol) and sulfuric acid (fuming, 3 drops). After heating to reflux with stirring for 16 h, the reaction mixture was cooled to RT and diluted with methylene chloride. The mixture was washed with a saturated solution of sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated to afford 7 g of methyl 4-(dimethoxymethyl)benzoate as a colorless oil.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux
  3. washThe mixture was washed with a saturated solution of sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-92cd2e88b2544081aed5e8ecd0eb3a72
Source dataset
uspto-grants-2014_05
Patent number
US08729110B1

Reaction notes

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