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

HRID 1690705Notes

Reaction equation

HRID 1690705 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:9][CH2:10][CH2:11][C:12]([C:6]1[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][C:4]=1[OH:5])=[O:13]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 78993-Chloropropionic acidHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 118057423-Chloro-1-(2,4-dihydroxyphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of resorcinol (5 g, 45.5 mmol) and 3-chloropropionic acid (5.2 g, 48 mmol), is added trifluoromethanesulfonic acid (25 g, 166 mmol) in one portion. The mixture is stirred at room temperature for 10 min, then heated at 80° C. for 30 min. The reaction is cooled to room temperature and the mixture is diluted with DCM (200 mL). The solution is slowly poured into ice water (200 mL). The bi-layer is separated, and the aqueous phase is extracted with DCM (2×40 mL). The combined organic phase is washed with brine and dried over sodium sulfate. The crude 3-chloro-1-(2,4-dihydroxy-phenyl)-propan-1-one is obtained as orange solid (6.9 g) after evaporation of solvent and carried on as is.

Workup

  1. temperatureheated at 80° C. for 30 min
  2. temperatureThe reaction is cooled to room temperature
  3. customThe bi-layer is separated
  4. extractionthe aqueous phase is extracted with DCM (2×40 mL)
  5. washThe combined organic phase is washed with brine
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-54de0088aa5642f6bb182ac76f7cab31
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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