Hydrochloric Acid → 10,10-Dioxo-9,10-dihydro-10lambda~6~-thioxanthene-3-carboxylic acid

HRID 1447566Notes

Reaction equation

HRID 1447566 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8](=O)[C:9]3[C:14]([S:15](=[O:19])(=[O:18])[C:16]=2[CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)([OH:3])=[O:2].Cl>C(O)(=O)C.[Zn]>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C:9]3[C:14]([S:15](=[O:19])(=[O:18])[C:16]=2[CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid3×HCID 401183-Carboxy-thioxanthone-10,10-dioxide

Product 1

HCID 2038418310,10-Dioxo-9,10-dihydro-10lambda~6~-thioxanthene-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

3-Carboxythioxanthone-10,10-dioxide (prepared as in Reference Preparation 4) (5.0 g), zinc wool (10.0 g) and mercuric acetate (0.2 g) in acetic acid (100 ml) were brought to the boil and concentrated hydrochloric acid (10 ml) was added. Vigorous evolution of hydrogen chloride occurred at first. After 2 hr., further hydrochloric acid (7 ml), was added and the mixture boiled under reflux for further 4 hr. It was then filtered while hot and poured on to ice and water. The precipitated product was filtered off and dried at 80° C. in vacuo, m.p. 229°-248° C. Two recrystallisations from methanol gave the product m.p. 254° C.

Workup

  1. additionwas added
  2. temperatureunder reflux for further 4 hr
  3. filtrationIt was then filtered while hot and
  4. additionpoured on to ice and water
  5. filtrationThe precipitated product was filtered off
  6. customdried at 80° C. in vacuo, m.p. 229°-248° C
  7. customTwo recrystallisations from methanol

Sources & evidence

ORD record
ord-2daf1724912b4ab2b3d06b9a8ee65a21
Source dataset
uspto-grants-1979_12
Patent number
US04177257

Reaction notes

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