p-Toluenesulfonic acid → HCID 53819662, compound

HRID 1758050Notes

Reaction equation

HRID 1758050 reaction equation
O[CH2:2][CH2:3][S:4][CH:5](C)[C:6](=[O:21])[C:7](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:21]1[C:6]([C:7](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][S:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53703915HCID 53703915, compound

Product 1

HCID 53819662HCID 53819662, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4-(2-hydroxyethylthio)-3-oxo-2-n-hexyloxyiminovalerate (300 g.), p-toluenesulfonic acid (42.0 g.) and toluene (2.5 l.) were treated in a similar manner to that of Example I-(ii) and refluxed under heating for 1.5 hours. The resultant solution was treated in a similar manner to that of Example I-(ii) to give ethyl 2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-n-hexyloxyiminoacetate (mixture of syn isomer and anti isomer, 186.8 g.).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 1.5 hours

Sources & evidence

ORD record
ord-fa3a04dc50d6435698bc73bd3f31b254
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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