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

HRID 1585730Notes

Reaction equation

HRID 1585730 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

Conditions

Temperature
80 °C

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 about 45 minutes at about 80° C. then cooled to room temperature over about 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. 1H-NMR (300 MHz, CDCl3): 12.56 (1H, s), 7.63 (1H, d, J=7.6 Hz), 6.37-6.46 (2H, m), 3.92 (2H, t, J=6.3 Hz), 3.41 (2H, t, J=6.3 Hz).

Workup

  1. temperaturethen cooled to room temperature over about 15 minutes
  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-8f24f3aa365448b58e4602ac53e4e1c6
Source dataset
uspto-grants-1999_08
Patent number
US05939452

Reaction notes

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