p-Toluenesulfonic acid → HCID 54149411, compound

HRID 1532952Notes

Reaction equation

HRID 1532952 reaction equation
[Na+].[Na+].[CH2:3]([O:5][P:6]([CH:11]([P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])/[C:12](=[CH:16]/[C:17]([O-:19])=[O:18])/[C:13]([O-:15])=O)([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:9]([O:8][P:6]([CH:11]([P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])[C:12]1[C:13]([O:19][C:17](=[O:18])[CH:16]=1)=[O:15])([O:5][CH2:3][CH3:4])=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 88162842HCID 88162842, compound

Product 1

HCID 54149411HCID 54149411, compoundYield 125.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.5 g of 2-[bis(diethoxyphosphoryl)methyl]maleic acid disodium salt in 50 ml of acetone is added with 2.13 g of para-toluenesulphonic acid. After 8 minutes under stirring, the formed sodium para-toluenesulphonate is separated by filtration and solvent is evaporated under reduced pressure. The residue is redissolved in 7.5 ml of anhydrous tetrahydrofuran and cooled to 0° C., then it is added dropwise with 3.8 ml of trifluoroacetic anhydride. The reaction mixture is refluxed for 30 minutes, then it is cooled to room temperature and concentrated to dryness. The residue is treated with ethyl ether, filtered and concentrated to dryness. This work up is repeated twice with toluene. 2.7 g of the product are obtained.

Workup

  1. customthe formed sodium para-toluenesulphonate is separated by filtration and solvent
  2. customis evaporated under reduced pressure
  3. dissolutionThe residue is redissolved in 7.5 ml of anhydrous tetrahydrofuran
  4. additionit is added dropwise with 3.8 ml of trifluoroacetic anhydride
  5. temperatureThe reaction mixture is refluxed for 30 minutes
  6. temperatureit is cooled to room temperature
  7. concentrationconcentrated to dryness
  8. additionThe residue is treated with ethyl ether
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-25d9be95dbd745febeaa19583154d237
Source dataset
uspto-grants-2001_03
Patent number
US06207655B1

Reaction notes

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