Hydrochloric Acid → HCID 22062850, compound

HRID 2075230Notes

Reaction equation

HRID 2075230 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[I-:16].[K+].II.Cl>[OH-].[NH4+].O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:6][C:7]=1[I:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 4875Potassium IodideHCID 143474-Hydroxybenzophenone

Product 1

HCID 22062850HCID 22062850, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A solution of (4-hydroxyphenyl)(phenyl)methanone (2.0 g, 10 mmol) in saturated aqueous ammonium hydroxide (130 mL) was stirred at 25° C. for 15 min, and then treated with a solution of potassium iodide (8.2 g, 49 mmol) and iodine (2.6 g, 10 mmol) in water (260 mL). After 30 min, the mixture was adjusted to pH 2 with concentrated aqueous HCl and extracted with EtOAc (500 mL). The organic extract was sequentially washed with sat. aqueous sodium thiosulfate (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (ISCO, 40 g, 0->80% EtOAc/hexanes) gave (4-hydroxy-3-iodophenyl)(phenyl)methanone as a white solid. MS (ESI) m/z: Calculated: 324.0; Observed: 325 (M++1).

Workup

  1. extractionextracted with EtOAc (500 mL)
  2. extractionThe organic extract
  3. washwas sequentially washed with sat. aqueous sodium thiosulfate (100 mL) and brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue (ISCO, 40 g, 0->80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-95c7f423775246a9af7c40c6a93d3dd4
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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