Chlorosulfonic acid → HCID 86743954, compound

HRID 1651140Notes

Reaction equation

HRID 1651140 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.[Cl:17][S:18](O)(=[O:20])=[O:19].[Cl-].[Ca+2].[Cl-]>>[Cl:17][S:18]([C:7]1[C:6]2[C:5](=[O:16])[C:4]3[C:13](=[CH:14][CH:15]=[C:2]([Cl:1])[CH:3]=3)[O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:20])=[O:19]

Participants

4

Reactant 3

HCID 24638Chlorosulfonic acidHCID 2555962-Chloro-9-xanthenoneHCID 5284359Calcium Chloride

Product 1

HCID 86743954HCID 86743954, compound

Conditions

Temperature
120 °C

Procedure

80 g (0.347 moles) of 2-chloroxanthone (DHAR, J. Chem. Soc. 117, 1068) are suspended in 210 ml of chlorosulfonic acid (368.1 g; 3.16 moles) in a 500 ml one neck flask provided with refluxing coolant and calcium chloride valve. The mixture is slowly heated in an oil bath up to 120° C. under magnetic stirring. It is maintained at 120°-130° C. until the gas development ceases (2-3 h). The cool reaction mixture is carefully dropwise added to a becker containing ground ice under mechanical stirring. A heavy crystalline product is separated which is filtered on Buchner and washed with iced H2O. It is dried in air. There are obtained 112 g (98%) of raw 2-(chlorosulfonyl-7-chloroxanthone. After TLC monitoring (silica gel F245 ; toluene, acetic acid 14:1, visualizer UV) the product is used as such for the next reaction.

Workup

  1. customprovided
  2. temperatureIt is maintained at 120°-130° C. until the gas development ceases (2-3 h)
  3. customThe cool reaction mixture
  4. additionis carefully dropwise added to a becker
  5. additioncontaining ground ice under mechanical stirring
  6. customA heavy crystalline product is separated which
  7. filtrationis filtered on Buchner
  8. washwashed with iced H2O
  9. customIt is dried in air

Sources & evidence

ORD record
ord-7143bc97a21f48a0bb520da8f6f5c723
Source dataset
uspto-grants-1990_05
Patent number
US04927849

Reaction notes

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