Reaction #6681

ord-424348839da04f94a84ae091f5ab15fa

Reaction equation

O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
BrCc1ccccc1
benzyl bromide
O=C(Cc1ccccc1)c1ccccc1
BzBn
CCOC(=O)c1ccc(O)cc1
ethyl 4-hydroxybenzoate
→
CCOC(=O)c1ccc(OCc2ccccc2)cc1
Ethyl 4-benzyloxybenzoate
Yield 100.0%

Reactants

O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
BrCc1ccccc1
benzyl bromide
O=C(Cc1ccccc1)c1ccccc1
BzBn
CCOC(=O)c1ccc(O)cc1
ethyl 4-hydroxybenzoate

Reagents

None

Solvents

CN(C)C=O
DMF
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe product was collected by extraction
  2. 2
    WashThe organic solution was washed with brine
  3. 3
    Dryingdried over MgSO4
  4. 4
    OtherAfter evaporation of solvent
  5. 5
    Otherpure product was obtained in yield of 100%

Procedure

35 mmol of benzyl bromide (BzBn, 35 mmol of ethyl 4-hydroxybenzoate (10), 14 g of Cs2CO3 and 40 ml of DMF were combined and stirred at RT ove night. Then the reaction mixture was poured into water and the product was collected by extraction. The organic solution was washed with brine and dried over MgSO4. After evaporation of solvent, pure product was obtained in yield of 100%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07083832B2uspto-grants-2006_08