Hydrochloric Acid → 4'-Phenylthio-2,4-dihydroxybenzophenone

HRID 1356483Notes

Reaction equation

HRID 1356483 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=2[OH:16])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>>[C:24]1([S:30][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]3[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=3[OH:16])=[CH:4][CH:3]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 519532(4-Chlorophenyl)(2,4-dihydroxyphenyl)methanone

Product 1

HCID 120842914'-Phenylthio-2,4-dihydroxybenzophenoneYield 108%

Conditions

Temperature
200 °C

Procedure

To 50 grams of 4′-chloro-2,4-dihydroxybenzophenone and 27.8 grams of potassium carbonate in 50 mL of 1-methyl-2-pyrrolidinone (NMP)is added 22.2 grams of thiophenol. The resulting suspension is heated at 200° C. with strrring for 2.5 hours. The reaction mixture is then allowed to cool to room temperature, made acidic with 10% aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water and brine, dried over anhydrous magnesium sulfate and concentrated to leave 70 grams of a deep red syrup. The crude material is dissolved in an ethyl acetate/heptane mixture (1:1) and partially purified by filtration through a bed of silica gel to yield after concentration 66.6 grams of a light orange solid; 1H NMR and IR data are consistent with the tide compound; Mass. Spec m/z 322 (M+).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c2670ec692f84f8eb7e236622aacb985
Source dataset
uspto-grants-2003_07
Patent number
US06586519B1

Reaction notes

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