Dimethylformamide → Benzyl 2-benzyloxy-5-formylbenzoate

HRID 454479Notes

Reaction equation

HRID 454479 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)[CH:17]=[O:18].C([C:22]1[CH:23]=[CH:24][C:25](O)=[C:26]([CH:30]=1)[C:27]([OH:29])=O)=O>C(OCC)(=O)C.O>[CH2:27]([O:29][C:8]1[CH:13]=[CH:12][C:11]([CH:17]=[O:18])=[CH:10][C:9]=1[C:1]([O:2][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4])[C:26]1[CH:30]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 692265-Formylsalicylic acid

Product 1

HCID 10405334Benzyl 2-benzyloxy-5-formylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (1.2 g) and benzyl bromide (0.79 mL) were sequentially added to an N,N-dimethylformamide (5 mL) solution of 5-formyl-2-hydroxybenzoic acid (0.50 g), followed by stirring at room temperature for 10 minutes and then at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, the solid substance was collected by filtration to obtain 0.93 g of benzyl 2-(benzyloxy)-5-formylbenzoate as a white solid.

Workup

  1. waitat 100° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the obtained residue
  8. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-f75e953452a74210826560867627f69f
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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