Dimethylformamide → Methyl 4-(benzyloxy)benzoate

HRID 976652Notes

Reaction equation

HRID 976652 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.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:23]([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:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 299810Methyl 4-(benzyloxy)benzoateYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-hydroxybenzoate (3.0 g, 19.7 mmole), potassium carbonate (2.8 g, 20.2 mole) and N,N-dimethylformamide (40 mL) was stirred at 70° C. for 2 hours. Benzyl bromide (2.38 mL, 20 mmole) was added and the reaction was maintained for an additional 18 hours. The mixture was cooled to ambient temperature and dissolved into water (400 mL). The aqueous phase was extracted with ethyl acetate (3×100 mL). The combined organic fractions were dried over magnesium sulfate, filtered and concentrated to provide 4.5 g of methyl 4-benzyloxybenzoate as a white powder, m.p. 96°-97° C.

Workup

  1. temperaturethe reaction was maintained for an additional 18 hours
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae987cefbfb34927aa26317aecfb8ff1
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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