Formic Acid → 4-Formyloxymethylbenzoic Acid

HRID 895643Notes

Reaction equation

HRID 895643 reaction equation
[CH:1]([OH:3])=[O:2].C(OC(=O)C)(=O)C.O[CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1>O>[CH:1]([O:3][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)=[O:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 763604-(Hydroxymethyl)benzoic acid

Product 1

HCID 223805554-Formyloxymethylbenzoic AcidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Formic acid (1.24 ml) and acetic anhydride (0.62 ml) were mixed and stirred at 50° C. for 30 minutes. This solution was cooled to 0° C., added with 4-hydroxymethylbenzoic acid (500 mg) and stirred at room temperature for 4.5 hours. The reaction mixture was added with water (5 ml) and extracted twice with ethyl acetate (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 536 mg of the title compound. Yield: 91%.

Workup

  1. temperatureThis solution was cooled to 0° C.
  2. stirringstirred at room temperature for 4.5 hours
  3. extractionextracted twice with ethyl acetate (5 ml)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-94c7bbf52dd74c55930762f1e30f7a93
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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