Pentaerythritol → p-Toluenesulfonic acid

HRID 982611Notes

Reaction equation

HRID 982611 reaction equation
C(O)C(CO)(CO)CO.[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:15][CH:16]=1.O>C1(C)C=CC=CC=1>[C:11]1([CH3:10])[CH:12]=[CH:13][C:14]([S:17]([OH:20])(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8285PentaerythritolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 157.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.2 g (0.54 mmol) of compound 9, 0.2 g (1.7 mmol) of 1,1,1-tris(hydroxymethyl)ethanol and 0.13 g (0.7 mmol) of p-TsOH.H2O in 30 mL of toluene was refluxed for 16 h, cooled to room temperature and filtered. The white solid product was isolated as a p-toluene sulfonic acid salt (0.19 g) (mass spec. MH+=470. Mpt.=223-226.5° C.).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationfiltered

Sources & evidence

ORD record
ord-52448132cf934667b40e5f6c517f2b01
Source dataset
uspto-grants-2005_03
Patent number
US06861423B2

Reaction notes

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