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

HRID 871216Notes

Reaction equation

HRID 871216 reaction equation
[C:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH3:12][O:11][C:9](=[O:10])[C:8]1[CH:13]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][C:7]=1[O:14][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

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

Product 1

HCID 12368981Benzoic acid, 5-acetyl-2-(phenylmethoxy)-, methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Methyl 5-acetylsalicylate (100 g, 0.515 mol) was dissolved in acetonitrile (1 L) in a 2 L flask under reflux conditions and a nitrogen atmosphere. Potassium carbonate (213.5 g, 1.545 mol) was added portion-wise over 15 min. Benzyl bromide (67.4 mL, 0.566 mol) was added using a dropping funnel over 15 min. The reaction was heated to 85° C. for 9 h, and then filtered and rinsed with acetonitrile (100 mL). The solution was concentrated to about 300 mL volume under reduced pressure and partitioned between water (1 L) and ethyl acetate (1 L). The organic layer was washed with saturated sodium chloride (250 mL), dried using magnesium sulfate (75 g), and then filtered and rinsed with ethyl acetate (100 mL). The organic layer was concentrated to give 2-benzyloxy-5-acetylbenzoic acid methyl ester as a solid (100% yield).

Workup

  1. customover 15 min
  2. filtrationfiltered
  3. washrinsed with acetonitrile (100 mL)
  4. concentrationThe solution was concentrated to about 300 mL volume under reduced pressure
  5. custompartitioned between water (1 L) and ethyl acetate (1 L)
  6. washThe organic layer was washed with saturated sodium chloride (250 mL)
  7. customdried
  8. filtrationfiltered
  9. washrinsed with ethyl acetate (100 mL)
  10. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-68d0496eabd549b2804f6d1d0a9eba14
Source dataset
uspto-grants-2015_03
Patent number
US08969571B2

Reaction notes

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