Monobenzone → Ethyl [4-(Benzyloxy)phenoxy]acetate

HRID 1824314Notes

Reaction equation

HRID 1824314 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5]Br)[CH3:2].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][O:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:21][CH:20]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 734886Ethyl [4-(Benzyloxy)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethylbromoacetate (4.17 g, 25 mmol) was added to a mixture of 4-benzyloxyphenol (5.00 g, 25 mmol) and K2CO3 (3.50 g, 25 mmol) in DMF (75 mL) and stirred for 20 hours at ambient temperature. The mixture was then concentrated in vacuo and the residue partitioned between water and EtOAc. The aqueous phase was further extracted with 2×50 mL of EtOAc and the combined extracts were washed with 2×50 mL of water and dried over Na2SO4. Concentration of the organic solution in vacuo left 7.00 g (97%) of product as a white solid. m.p. 65–68° C.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. extractionThe aqueous phase was further extracted with 2×50 mL of EtOAc
  4. washthe combined extracts were washed with 2×50 mL of water
  5. dry with materialdried over Na2SO4
  6. waitConcentration of the organic solution in vacuo left 7.00 g (97%) of product as a white solid

Sources & evidence

ORD record
ord-cc7e780f1cb74adbb1ae480bb4a24718
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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