p-Toluenesulfonic acid → p-Toluenesulfonic acid

HRID 335383Notes

Reaction equation

HRID 335383 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1>CC(OC)(C)C>[CH4:1].[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 6101p-Toluenesulfonic acid

Product 2

HCID 297MethaneHCID 6101p-Toluenesulfonic acidYield 665.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
20 °C

Procedure

A reactor was charged at about 20° C. with the compound of formula (I) form A0 (6.075 kg; 1 eq) and dichloromethane (92 L; 15 V). The mixture was stirred (80 rpm) at 20° C. for 15 minutes. After cooling the mixture to 10° C., paratoluene sulfonic acid (PTSA—2.417 kg; 1 eq) was added portion wise. The mixture was stirred at 80 rpm at 10° C. for 1 hour. Then, MTBE (122 L; 15 V) was added portion wise via a feed vessel. The mixture was heated to 45° C. at least 1 h (checking that the reaction was complete by RX/DSC, if it is necessary, continue the contact). After cooling the mixture to 10° C., the precipitated solids were isolated by filtration and washed with MTBE. The product was dried under vacuum at 40° C. to yield the addition salt of compound of formula (I) with PTSA (8.045 kg; yield=97.3%; purity=99.1%).

Workup

  1. temperatureAfter cooling the mixture to 10° C.
  2. stirringThe mixture was stirred at 80 rpm at 10° C. for 1 hour
  3. temperatureThe mixture was heated to 45° C. at least 1 h (checking that the reaction
  4. temperatureAfter cooling the mixture to 10° C.
  5. customthe precipitated solids were isolated by filtration
  6. washwashed with MTBE
  7. customThe product was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-886ebd7ddb53416091e12d75df5e5a7f
Source dataset
uspto-grants-2014_11
Patent number
US08884014B2

Reaction notes

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