Hydrochloric Acid → 4-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyric Acid Ethyl Ester

HRID 11621Notes

Reaction equation

HRID 11621 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:15])=[C:6]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:7]=1.Cl.[CH2:17](O)[CH3:18]>>[CH2:17]([O:12][C:11](=[O:13])[CH2:10][CH2:9][C:8]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:15])=[O:14])[CH3:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 41452424-(5-Chloro-2-hydroxyphenyl)-4-oxobutanoic acid

Product 1

HCID 684473744-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyric Acid Ethyl Ester

Procedure

A solution of 4-(5-chloro-2-hydroxy-phenyl)-4-oxo-butyric acid (0.25 g, 1.09 mmol) in ethanol (10 mL) saturated with hydrogen chloride (g) was stirred at ambient temperature for 12 hours. The reaction was concentrated in vacuo, dissolved in diethyl ether and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (0.259 g).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutiondissolved in diethyl ether
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44dafea2b06842acb7dacd01a2391aa6
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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