Ethyl Acetate → Ethyl 2-(4-hydroxyphenyl)-2-oxoacetate

HRID 1071778Notes

Reaction equation

HRID 1071778 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.C(OCC)(=O)C>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 111357Benzeneacetic acid, alpha,4-dihydroxy-, ethyl ester

Product 1

HCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateYield 27.2%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

15.3 g of chromium trioxide is added dropwise to a solution of 15 g of ethyl 4-hydroxymandelate in 240 ml of acetic acid. The mixture is stirred at room temperature for 2 hours, poured into 1 l of ethyl acetate and extracted with saturated aqueous Na2CO3 solution. The aqueous phases are extracted with methylene chloride. The organic phases are washed with saturated aqueous Na2CO3 solution, followed by washing with water. The organic phases are dried over sodium sulfate. Filtration, evaporation of the solvent and distillation (ball-tube still distillation, boiling point 205° C. (0.076 bar)) give 4.04 g (27 wt %) ethyl 4-hydroxybenzoylformate as a yellow solid.

Workup

  1. extractionextracted with saturated aqueous Na2CO3 solution
  2. extractionThe aqueous phases are extracted with methylene chloride
  3. washThe organic phases are washed with saturated aqueous Na2CO3 solution
  4. washby washing with water
  5. dry with materialThe organic phases are dried over sodium sulfate
  6. filtrationFiltration, evaporation of the solvent and distillation (ball-tube
  7. distillationstill distillation, boiling point 205° C. (0.076 bar))

Sources & evidence

ORD record
ord-9d5c3f3b648f409084cf2952c3aaf932
Source dataset
uspto-grants-2005_06
Patent number
US06906113B2

Reaction notes

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