Benzyl Bromide → Benzyl 2-benzyloxy-5-formylbenzoate

HRID 644399Notes

Reaction equation

HRID 644399 reaction equation
[CH:1]([C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1)=[O:2].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:13]([O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:3]([CH:1]=[O:2])[CH:4]=[CH:5][C:6]=1[O:12][CH2:1][C:3]1[CH:11]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 692265-Formylsalicylic acid

Product 1

HCID 10405334Benzyl 2-benzyloxy-5-formylbenzoateYield 115.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-formylsalicylic acid (4.98 g, 30 mmol), benzyl bromide (15.39 g, 90 mmol), potassium carbonate (16.59 g, 120 mmol), and methyl ethyl ketone (350 mL) was refluxed for 8 hours. After cooling, the solvent was evaporated under reduced pressure. 2N Hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate. The layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1), suspended and washed with isopropyl ether under heating at reflux to give the title compound (5.98 g, 57.5%) as a white solid.

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under reduced pressure
  4. addition2N Hydrochloric acid was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe residue obtained by evaporation of the solvent under reduced pressure
  9. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1)
  10. washwashed with isopropyl ether
  11. temperatureunder heating
  12. temperatureat reflux

Sources & evidence

ORD record
ord-a691eae9757f4d9ca63a0a7be3e30c2b
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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