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

HRID 2384348Notes

Reaction equation

HRID 2384348 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+]>CC(CC)=O>[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 methylethylketone (350 mL) was refluxed for 8 hours. After cooling, the solvent was evaporated under reduced pressure. 2 N 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. addition2 N 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-b68860bbea98480fa36319718648deed
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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