Benzyl Bromide → Benzoic acid, 5-acetyl-2-(phenylmethoxy)-, methyl ester

HRID 644405Notes

Reaction equation

HRID 644405 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)[OH:6].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[CH:8]=[CH:7][C:5]=1[O:6][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 12368981Benzoic acid, 5-acetyl-2-(phenylmethoxy)-, methyl esterYield 71.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-acetylsalicylic acid methyl ester (13.59 g, 70 mmol), benzyl bromide (17.96 g, 105 mmol), potassium carbonate (19.35 g, 140 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 it was extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated, the residue was recrystallized from isopropyl ether to give the title compound (14.20 g, 71.4%) 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, and it
  5. extractionwas extracted with ethyl acetate
  6. washAfter the ethyl acetate layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customthe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-189be7c814b34ef484c25ee1d7da93da
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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