p-Toluenesulfonic acid → HCID 59804969, compound

HRID 604845Notes

Reaction equation

HRID 604845 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([P:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=[CH:11][CH:12]=2)OCC[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[C:2]([C:7]1[CH:8]=[C:9]([P:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 59804955HCID 59804955, compound

Product 1

HCID 59804969HCID 59804969, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

25.7 g (73.9 mmol) of [3-(2-methyl-1,3-dioxolane-2-yl)phenyl]diphenylphosphane are dissolved under cover gas in 240 mL of a THF/water mixture (1:1) and mixed with 0.9 g of 4-toluenesulphonic acid. The mixture is boiled under reflux until the original compound is completely reacted. After the addition of 50 mL of a degassed 0.5 M NaHCO3 solution it is washed and after extraction with degassed toluene, the organic phase is separated off and dried over anhydrous MgSO4. The solvent is removed at the rotary evaporator and the residue is purified by column chromatography. The product is obtained in a yield above 70% as colorless oil (purity: >98%, GC). C20H17OP.

Workup

  1. temperatureunder reflux until the original compound
  2. customis completely reacted
  3. washis washed
  4. extractionafter extraction with degassed toluene
  5. customthe organic phase is separated off
  6. dry with materialdried over anhydrous MgSO4
  7. customThe solvent is removed at the rotary evaporator
  8. customthe residue is purified by column chromatography
  9. customThe product is obtained in a yield above 70% as colorless oil (purity: >98%, GC)

Sources & evidence

ORD record
ord-bc29db33ab084e9a8f51f2c9eef23a1c
Source dataset
uspto-grants-2011_03
Patent number
US07910744B2

Reaction notes

Loading…