Chlorosulfonic acid → HCID 23051703, compound
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:8]1[CH:9]=[CH:10][C:11]2[O:12][C:13]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=3)[C:5](=[O:16])[C:6]=2[CH:7]=1)(=[O:20])=[O:19]Participants
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
- customprovided
- temperatureIt is maintained at 120°-130° C. until the gas development ceases (2-3 h)
- customThe cool reaction mixture
- additionis carefully dropwise added to a becker
- additioncontaining ground ice under mechanical stirring
- customA heavy crystalline product is separated which
- filtrationis filtered on Buchner
- washwashed with iced H2O
- customIt is dried in air
Sources & evidence
- ORD record
- ord-358aacb4ffa345388911f46f0eef9ee6
- Source dataset
- uspto-grants-1991_11
- Patent number
- US05066676
Reaction notes
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