Resorcinol → 3-Chloro-1-(2,4-dihydroxyphenyl)propan-1-one

HRID 741722Notes

Reaction equation

HRID 741722 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[Cl:9][CH2:10][CH2:11][C:12](O)=[O:13].FC(F)(F)S(O)(=O)=O.C(Cl)(Cl)Cl>O>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:12](=[O:13])[CH2:11][CH2:10][Cl:9]

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 6212ChloroformHCID 78993-Chloropropionic acidHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 118057423-Chloro-1-(2,4-dihydroxyphenyl)propan-1-oneYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of resorcinol (200 g, 1.82 mol) and 3-chloropropionic acid (200 g, 1.84 mol) was added trifluoromethane sulfonic acid (1 kg) in one portion. The solution was heated slowly over 45 minutes to 80° C. then cooled to room temperature over 15 minutes and poured into chloroform (4.0 L). The organic portion was slowly poured into water (4.0 L) and the layers separated. The aqueous layer was extracted with chloroform (2×2.0 L). The combined organic layers were washed with brine, dried over sodium sulfate and filtered. Concentration in vacuo gave an orange semi-solid (244.1 g) which was used crude in the next step.

Workup

  1. temperatureThe solution was heated slowly over 45 minutes to 80° C.
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with chloroform (2×2.0 L)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-7228ecb2c4b8438a8b385643b87d74c7
Source dataset
uspto-grants-1996_09
Patent number
US05552435

Reaction notes

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