Hydrochloric Acid → 2-Phenoxathiincarboxylic acid

HRID 614496

Reaction equation

HRID 614496 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=1)(=[O:3])C.Cl[O-:19].[Na+].[OH-].[Na+].Cl>O1CCOCC1>[CH:5]1[C:6]2[S:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[O:14][C:15]=2[CH:16]=[CH:17][C:4]=1[C:1]([OH:3])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5151742-AcetylphenoxathiinHCID 23665760Sodium Hypochlorite

Product 1

HCID 8200622-Phenoxathiincarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-acetylphenoxathiin (4.80 g), sodium hypochlorite solution (95 ml; 5.7% available chlorine), 4% sodium hydroxide solution (100 ml) and dioxan (100 ml) was mechanically stirred on the steam bath for 5 hrs,. The solution was poured on to ice and excess hydrochloric acid with stirring. The white precipitate was filtered off and dissolved in hot 4% sodium hydroxide solution (40 ml) and filtered. The sodium salt of the required acid crystallised from the filtrate on cooling and was filtered off, dissolved in boiling water, and the acid precipitated by addition of excess hydrochloric acid. It was filtered off and recrystallised from acetic acid, m.p. 253° C.

Workup

  1. stirringwith stirring
  2. filtrationThe white precipitate was filtered off
  3. dissolutiondissolved in hot 4% sodium hydroxide solution (40 ml)
  4. filtrationfiltered
  5. customThe sodium salt of the required acid crystallised from the filtrate
  6. temperatureon cooling
  7. filtrationwas filtered off
  8. dissolutiondissolved
  9. customthe acid precipitated by addition of excess hydrochloric acid
  10. filtrationIt was filtered off
  11. customrecrystallised from acetic acid, m.p. 253° C.

Sources & evidence

ORD record
ord-d691c5b0b14f40839f8cfa72f6968c72
Source dataset
uspto-grants-1979_03
Patent number
US04145350

Linked notes

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