2-Chloro-1-(5-chloro-2-hydroxyphenyl)ethanone → 5-Chloro-2,3-dihydro-1-benzofuran-3-one

HRID 2177016Notes

Reaction equation

HRID 2177016 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[OH:12])=[O:4].C([O-])(=O)C.[Na+]>C(O)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]2[O:12][CH2:2][C:3](=[O:4])[C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 2371292-Chloro-1-(5-chloro-2-hydroxyphenyl)ethanoneHCID 517045Sodium Acetate

Product 1

HCID 37113525-Chloro-2,3-dihydro-1-benzofuran-3-oneYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

(Ref: J. Org. Chem. 1955; 20; 813-818) A solution of 2-chloro-1-(5-chloro-2-hydroxy-phenyl)-ethanone (5 g; 24.4 mmol) in ethanol was heated to reflux for 10 minutes and sodium acetate (2 g; 24.4 mmol) was added to the hot mixture. Mixture continued to reflux an additional 10 minutes, and reaction was stoppered and chilled to 0° C. for 20 minutes. Mixture was quenched with water and mixture extracted with ethyl acetate (3×75 mL). Combined organics was washed with brine and dried over MgSO4. Crude material was purified by chromatography using 0-1% methanol/DCM to afford 5-chlorobenzofuran-3-one as a oily solid. (3.0 g; 75% yield).

Workup

  1. temperatureto reflux for 10 minutes
  2. temperatureto reflux an additional 10 minutes
  3. customreaction
  4. customMixture was quenched with water and mixture
  5. extractionextracted with ethyl acetate (3×75 mL)
  6. washCombined organics was washed with brine
  7. dry with materialdried over MgSO4
  8. customCrude material was purified by chromatography

Sources & evidence

ORD record
ord-bcd0f018e40246a9a9df07d054f6e94d
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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