Methylparaben → Methyl 4-(benzyloxy)benzoate

HRID 1387752Notes

Reaction equation

HRID 1387752 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>CN(C)C=O.CCCCC>[CH2:18]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][CH:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 299810Methyl 4-(benzyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8003PentaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 15.2 g of methyl4-hydroxybenzoate (100 mmol) in 125 mL of N,N-dimethylformamide was added under stirring 33.13 g of potassium carbonate (240 mmol). Then 17.45 g of benzyl bromide (102 mmol) was added within 5 minutes. The mixture was stirred at 25° C. using a water bath. The reaction was complete after 3 hours. The reaction mixture was poured into a mixture of 180 g of ice and 200 mL of ethyl acetate. After extraction, the aqueous phase was separated and extracted with three portions of 80 mL of ethyl acetate. The organic phase was washed with two portions of 150 mL of water, combined, dried (MgSO4) and partially concentrated to give a thick suspension. 60 mL of pentane was added and the suspension was stirred during 2 hours at room temperature. The crystalline methyl 4-benzyloxybenzoate was collected on a filter, washed with pentane and dried.

Workup

  1. extractionAfter extraction
  2. customthe aqueous phase was separated
  3. extractionextracted with three portions of 80 mL of ethyl acetate
  4. washThe organic phase was washed with two portions of 150 mL of water
  5. dry with materialdried (MgSO4)
  6. concentrationpartially concentrated
  7. customto give a thick suspension
  8. stirringthe suspension was stirred during 2 hours at room temperature
  9. customThe crystalline methyl 4-benzyloxybenzoate was collected on a filter
  10. washwashed with pentane
  11. customdried

Sources & evidence

ORD record
ord-6572681d9b8e459db85efe59cc230e77
Source dataset
uspto-grants-2001_07
Patent number
US06268499B1

Reaction notes

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