Hydrogen Peroxide → 2-Carboxyphenoxathiin-10-oxide

HRID 372487Notes

Reaction equation

HRID 372487 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]([OH:17])=[O:16].[OH:18]O>C(O)C>[C:15]([C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:13](=[O:18])[C:14]=2[CH:1]=1)([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 8200622-Phenoxathiincarboxylic acid

Product 1

HCID 203277292-Carboxyphenoxathiin-10-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenoxathiin-2-carboxylic acid (0.61g) was dissolved in refluxing absolute ethanol (40 ml) and 30% w/v hydrogen peroxide solution (1.50 ml) added. Reflux was maintained for 2 hours, more 30% w/v hydrogen peroxide solution (1.00 ml.) added, and reflux continued for 17 hours. The solution was evaporated to low volume, and the product crystallised out. The solid was filtered, washed and dried to give 2-carboxyphenoxathiin-10-oxide m.p. 223° C. Recrystallisation from absolute ethanol raised the melting point to 237° C.

Workup

  1. additionadded
  2. temperatureReflux
  3. temperaturewas maintained for 2 hours
  4. additionadded
  5. temperaturereflux
  6. customThe solution was evaporated to low volume
  7. customthe product crystallised out
  8. filtrationThe solid was filtered
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-80a36d2874b643b1b071bb17972b06a1
Source dataset
uspto-grants-1978_05
Patent number
US04091108

Reaction notes

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