Acetic Acid → 1-(5-Chloro-2,4-dihydroxyphenyl)ethan-1-one

HRID 1891135Notes

Reaction equation

HRID 1891135 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([OH:10])=[CH:8][C:7]=1[OH:13].C([O-])(=O)C.[Na+]>B(F)(F)F.CCOCC>[Cl:5][C:6]1[C:7]([OH:13])=[CH:8][C:9]([OH:10])=[C:11]([C:1](=[O:4])[CH3:2])[CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 17314-ChlororesorcinolHCID 517045Sodium Acetate

Product 1

HCID 172451191-(5-Chloro-2,4-dihydroxyphenyl)ethan-1-oneYield 58%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Conditions

Temperature
90 °C

Procedure

Acetic acid (17.5 mL) was added dropwise to a suspension of 4-chlororesorcinol (42.5 g, 0.293 mmol) in boron trifluoride etherate (200 mL) under a nitrogen atmosphere. The reaction mixture was heated at 90° C. for 3.5 hours and then allowed to cool to room temperature. A solid had formed after around 1 hour of cooling. The mixture was poured into 700 mL of a 10% w/v aqueous sodium acetate solution. This mixture was stirred vigorously for 2.5 hours. A light brown solid had formed which was filtered, washed with water and air-dried overnight to afford 1-(5-chloro-2,4-dihydroxy-phenyl)-ethanone (31.6 g, 58%). LCMS: [M−H]+ 185.

Workup

  1. temperatureto cool to room temperature
  2. customA solid had formed after around 1 hour
  3. temperatureof cooling
  4. customA light brown solid had formed which
  5. filtrationwas filtered
  6. washwashed with water
  7. customair-dried overnight

Sources & evidence

ORD record
ord-27c841d5bb1c470fb82734bd50ff4e5e
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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