Water → p-Tolyl methyl sulfone

HRID 26688

Reaction equation

HRID 26688 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([O-:9])=[O:8])=[CH:3][CH:2]=1.[Na+].[CH2:12](N(CC)CC)C.O>CP(OC)(=O)OC>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([CH3:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 18521p-Tolyl methyl sulfoneYield 81.1%

Reagents, catalysts & solvents 1

HCID 12958Dimethyl methylphosphonateSolvent

Conditions

Temperature
171 °C

Procedure

A suspension of 22.7 g of sodium p-toluenesulphinate in 50 ml of dimethyl methanephosphonate is treated with 12.6 g of triethylamine and the mixture is heated in the course of 45 minutes to 167° C. The temperature is raised further to 171° C. and kept thereat for a further 30 minutes. The cooled solution is poured into 700 ml of water and stired for 1 hour. The precipitated crystalline product is collected by filtration and washed with 350 ml of water. The residue is dried at 25 torr and 50° C., affording 17.2 g (80.9% of theory) of p-tolylmethylsulphone of the formula ##STR14## with a melting point of 85°-96° C. and a purity of 95.8%.

Workup

  1. temperaturethe mixture is heated in the course of 45 minutes to 167° C
  2. waitstired for 1 hour
  3. filtrationThe precipitated crystalline product is collected by filtration
  4. washwashed with 350 ml of water
  5. customThe residue is dried at 25 torr and 50° C.

Sources & evidence

ORD record
ord-e61af428fdb94cdeb327be221c10d5d9
Source dataset
uspto-grants-1979_04
Patent number
US04151210

Linked notes

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