Methylparaben → Methyl 4-(benzyloxy)benzoate

HRID 1500991Notes

Reaction equation

HRID 1500991 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 299810Methyl 4-(benzyloxy)benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-hydroxybenzoate (1.37 g, 9 mmol) and (bromomethyl)benzene (1.71 g, 10 mmol) in acetonitrile (100 mL) was added potassium carbonate (2.76 g, 18.8 mmol). The reaction mixture was stirred at 60° C. for 2 hours. After the reaction, the solvent was removed under reduced pressure to give the crude product which was purified by column chromatography (silica gel, dichloromethane/methanol=100:1) to give the pure product (2.18 g, 99%). LRMS (M+H+) m/z: calcd 243.09. found 243.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed under reduced pressure
  3. customto give the crude product which
  4. customwas purified by column chromatography (silica gel, dichloromethane/methanol=100:1)

Sources & evidence

ORD record
ord-749c914aa9a24ed4a1bd4ea671560e8e
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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