Benzyl Chloride → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 62854

Reaction equation

HRID 62854 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Hydroxy-phenyl)-acetic acid methyl ester (1.0 g, 6.02 mmol) was dissolved in DMF (10 mL), and K2CO3(2.5 g, 18.06 mmol) was added thereto. Benzyl chloride (0.83 mL, 7.22 mmol) was added slowly thereto, and the mixture was stirred at 40˜50° C. for 12 hours. The reactant was cooled and concentrated under reduced pressure. The residue was added with water and then extracted with EtOAc. The organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography (eluent, EtOAc/Hex=1/4) to obtain the title compound (1.4 g, 91%).

Workup

  1. temperatureThe reactant was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was added with water
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (eluent, EtOAc/Hex=1/4)

Sources & evidence

ORD record
ord-71af20cbfa714d0c9ff47fe7831bd641
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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