Ethyl bromoacetate → Ethyl 2,4-dibenzyloxyphenoxyacetate

HRID 322995Notes

Reaction equation

HRID 322995 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[O:23][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 106383482,4-Dibenzyloxyphenol

Product 1

HCID 10763088Ethyl 2,4-dibenzyloxyphenoxyacetateYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-dibenzyloxyphenol (3.1 g) and sodium hydride (0.44 g, 60% dispersion in mineral oil) in THF (75 mL) is refluxed for 30 minutes then refluxing is allowed to abate. Neat ethyl bromoacetate (1.8 g) is added and refluxing continued for 1 hour. The reaction is concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase is washed with water (100 mL), dried o ver magnesium sulphate, filtered and concentrated in vacuo to give a light brown oil. Flash chromatography of the residue eluting with dichloromethane affords ethyl 2,4-dibenzyloxyphenoxyacetate (3.2 g) after trituration with pentane.

Workup

  1. temperatureis refluxed for 30 minutes
  2. temperaturethen refluxing
  3. temperaturerefluxing
  4. concentrationThe reaction is concentrated in vacuo
  5. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  6. washThe organic phase is washed with water (100 mL)
  7. dry with materialdried o ver magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a light brown oil
  11. washFlash chromatography of the residue eluting with dichloromethane

Sources & evidence

ORD record
ord-406da50b6949415cad03e327b79d0992
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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