p-Toluenesulfonic acid → HCID 22901798, compound

HRID 1489488Notes

Reaction equation

HRID 1489488 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C([O:16][C:17]1[CH:22]=[CH:21][C:20]([S+:23]([C:35]2[CH:40]=[CH:39][C:38]([O:41]C(C)(C)C)=[CH:37][CH:36]=2)[C:24]2[CH:29]=[CH:28][C:27]([O:30]C(C)(C)C)=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([S+:23]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 21872588HCID 21872588, compound

Product 1

HCID 22901798HCID 22901798, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6.5 g (0.01 mol) of tris(p-tert-butoxyphenyl)sulfonium p-toluenesulfonate and 0.95 g (0.005 mol) of p-toluenesulfonic acid in 40 g of methanol was heated at 60° C. for 7 hours with stirring. The reaction mixture was evaporated in vacuo. The residual oil was washed two times with 200 g of diethyl ether. The amount of this crude product was 4.7 g (97% yield). Without further purification, the crude product was used in subsequent reaction.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. washThe residual oil was washed two times with 200 g of diethyl ether
  3. customWithout further purification
  4. customthe crude product was used in subsequent reaction

Sources & evidence

ORD record
ord-8a663b07b2654de4be4648ea2f1e78e0
Source dataset
uspto-grants-1997_10
Patent number
US05679496

Reaction notes

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