Water → 4-(Benzenesulfonyl)benzaldehyde

HRID 1351661Notes

Reaction equation

HRID 1351661 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].F[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.O>CS(C)=O>[C:1]1([S:7]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 680234-FluorobenzaldehydeHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 144174774-(Benzenesulfonyl)benzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium phenylsulfinate (16.4 g, 0.1 mol) and 4-fluorobenzaldehyde (12.4 g, 0.1 mol) were combined in dimethylsulfoxide (100 mL) and heated at 120° C. for 4 days. The cooled reaction was poured into water. The resulting crystals were filtered off and washed with water, then dissolved in ethyl acetate/dichloromethane, dried and concentrated in vacuo until crystallisation ensued. The mixture was diluted with isohexane and the crystals filtered off and washed with further isohexane to yield 4-(phenylsulfonyl)benzaldehyde (19.6 g, 80%). δH (500 MHz, d6 DMSO): 10.06 (1H, s), 8.16 (2H, d, J=8.3 Hz), 8.09 (2H, d, J=8.3 Hz), 7.99 (2H, d, J=7.7 Hz), 7.71 (1H, t, J=6.9 Hz), 7.63 (2H, t, J=7.7 Hz).

Workup

  1. customThe cooled reaction
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate/dichloromethane
  5. customdried
  6. concentrationconcentrated in vacuo until crystallisation
  7. additionThe mixture was diluted with isohexane
  8. filtrationthe crystals filtered off
  9. washwashed with further isohexane

Sources & evidence

ORD record
ord-12dd35b107be4942ac7a16e93db2dc58
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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