Monobenzone → Methyl 2-[4-(benzyloxy)phenoxy]butanoate

HRID 1593542Notes

Reaction equation

HRID 1593542 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:23]([CH2:28][CH3:29])[C:24]([O:26][CH3:27])=[O:25]>CC#N>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:23]([CH2:28][CH3:29])[C:24]([O:26][CH3:27])=[O:25])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 10796Cesium carbonateHCID 95577Butanoic acid, 2-bromo-, methyl ester

Product 1

HCID 68566999Methyl 2-[4-(benzyloxy)phenoxy]butanoateYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-benzyloxyphenol (30 g, 0.15 mol), cesium carbonate (58.6 g, 0.18 mol) and methyl 2-bromobutanoate (40.7 g, 0.22 mol) in CH3CN (350 mL) was kept at reflux for 20 hr. After cooling, the mixture was filtered and concentrated under reduced pressure and chromatographed over silica gel using AcOEt/hexanes to give the title compound 41.0 g (91%).

Workup

  1. temperatureat reflux for 20 hr
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed over silica gel

Sources & evidence

ORD record
ord-d6db58e0762f4d45962d68995492031f
Source dataset
uspto-grants-2007_11
Patent number
US07297715B2

Reaction notes

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