Ethanol → Ethyl 3-(2-Bromo-3-formylphenoxy)propanoate

HRID 561838Notes

Reaction equation

HRID 561838 reaction equation
[Br:1][C:2]1[C:13]([CH:14]=[O:15])=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:21][CH2:22]O>>[Br:1][C:2]1[C:13]([CH:14]=[O:15])=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH2:5][CH2:6][C:7]([O:9][CH2:21][CH3:22])=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 866359223-(2-Bromo-3-formylphenoxy)propanoic acid

Product 1

HCID 86635923Ethyl 3-(2-Bromo-3-formylphenoxy)propanoate

Procedure

To a solution of 3-(2-bromo-3-formylphenoxy)propanoic acid from the previous step (I eq.) in EtOH (0.13 M) was added conc. sulfuric acid (0.8 eq.). The reaction was heated at reflux for 30 min. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic extracts were washed with water and sat. aq. NaHCO3. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the title compound as a yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 30 min
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with water and sat. aq. NaHCO3
  6. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-4eb173b7fb4341ba88696b8add55b4c1
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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