Water → Methyl 3-[4-(benzyloxy)phenyl]propanoate

HRID 2101784Notes

Reaction equation

HRID 2101784 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[C:16]1([CH2:15][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

HCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A reaction mixture of methyl 3-(4-hydroxyphenyl)propanoate (commercially available, from Aldrich) (4.0 g, 22 mmol), 1-(bromomethyl)benzene (3.8 g, 22 mmol (commercially available from Aldrich)) and cesium carbonate (14.30 g, 44 mmol) in DMSO (20.0 mL) was stirred at room temperature for 2.5 hours. The reaction mixture was poured into water (50.0 mL) and extracted with EtOAc (100.0 mL), and the organic layer was washed with water (3×30 mL) and brine (30 mL), and dried with MgSO4. The crude product was recrystallized with hexane/EtOAc (98/2) to the title compound 23.1. 1H NMR (500 MHz, CDCl3) δ ppm 2.65 (t, J=7.83 Hz, 2H) 2.94 (t, J=7.83 Hz, 2H) 3.71 (s, 3H) 5.08 (s, 2H) 6.95 (d, J=8.56 Hz, 2H) 7.16 (d, J=8.56 Hz, 2H) 7.34-7.50 (m, 5H).

Workup

  1. extractionextracted with EtOAc (100.0 mL)
  2. washthe organic layer was washed with water (3×30 mL) and brine (30 mL)
  3. dry with materialdried with MgSO4
  4. customThe crude product was recrystallized with hexane/EtOAc (98/2) to the title compound 23.1

Sources & evidence

ORD record
ord-9235f7f6fcaf4de5a1e448b2aeaabfd0
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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