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

HRID 1453202Notes

Reaction equation

HRID 1453202 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:15][O:16][C:17](=[O:27])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>CC(C)=O>[CH3:15][O:16][C:17](=[O:27])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (12.9 mL, 108 mmol), K2CO3 (15.0 g, 109 mmol) and the 3-(4-hydroxyphenyl)propionic acid methyl ester from Step 1 above were combined in acetone (300 mL) and refluxed 40 h. The crude reaction mixture was filtered and the cake washed with acetone (2×100 mL). The filtrate was evaporated and the residue was triturated with MeOH (50 mL, 6 mL, 4 mL) to provide the product as a solid which was used without further purification.

Workup

  1. temperaturerefluxed 40 h
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. washthe cake washed with acetone (2×100 mL)
  5. customThe filtrate was evaporated
  6. customthe residue was triturated with MeOH (50 mL, 6 mL, 4 mL)

Sources & evidence

ORD record
ord-f06efc807c7a414695c538438c99c265
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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