Water → Cyclohexyl benzenesulfonylacetate

HRID 129377Notes

Reaction equation

HRID 129377 reaction equation
Br[CH2:2][C:3]([O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:4].O.O.[C:14]1([S:20]([O-:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+].O>CS(C)=O>[C:14]1([S:20]([CH2:2][C:3]([O:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)=[O:4])(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 221279Cyclohexyl bromoacetateHCID 23681562Benzenesulfinic acid, sodium salt, dihydrate

Product 1

HCID 22908638Cyclohexyl benzenesulfonylacetateYield 76.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of cyclohexyl bromoacetate (15.6 g, 0.0705 mole) in dimethylsulfoxide (120 ml), sodium benzenesulfinate dihydrate (15 g, 0.075 mole) was added in a small portion at 20°-40° C., and reacted with stirring at 60° C. for 6 hours. After cooling, the reaction mixture was poured into cold H2O (1.5 liter). The precipitate was filtered, washed with H2O and dried to give 15.3 g of cyclohexyl benzenesulfonylacetate as a white crystals having a melting point of 35°-38° C.

Workup

  1. customreacted
  2. temperatureAfter cooling
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-4252bea07fb84a6fb565da9732a3bb8e
Source dataset
uspto-grants-1995_11
Patent number
US05468589

Reaction notes

Loading…