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

HRID 2119827Notes

Reaction equation

HRID 2119827 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-0df8950e2cca47ffaefe3e5ba7e76d52
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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