Water → HCID 21701225, compound

HRID 229202Notes

Reaction equation

HRID 229202 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>C1C=CC=CC=1>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 21476637HCID 21476637, compound

Product 1

HCID 21701225HCID 21701225, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of [4-(Methyloxy)phenyl][4-(methylsulfonyl)phenyl]methanone (92) (0.20 g, 0.69 mmol) and aluminum chloride (0.38 g, 2.76 mmol) were refluxed in benzene (10 mL) for 2 h and then cooled to 0° C. in an ice bath. Water (10 mL) was added slowly, and the mixture was extracted with EtOAc (2×75 mL). The combined organic extract was washed with water, brine, and dried over Na2SO4. Concentration of the extract gave the title compound (93) as light brown solid (0.19 g, 100%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 3.28 (s, 3H), 6.89 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.8 Hz, 2H), 7.85 (d, J=8.2 Hz, 2H), 8.05 (d, J=8.2 Hz, 2H), 10.56 (s, 1H). LCMS (ES): m/z 277 (M+H)+, m/z 275 (M−H)−.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×75 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-fb826b6276e14371ad0ab3a153caa480
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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