Chlorosulfonic acid → HCID 22558273, compound

HRID 2119943Notes

Reaction equation

HRID 2119943 reaction equation
[CH2:1]([C:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:9]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:43][S:44]([OH:47])(=O)=[O:45]>ClCCl>[CH2:1]([C:7]1[C:8]([C:37]2[CH:42]=[CH:41][C:40]([S:44]([Cl:43])(=[O:47])=[O:45])=[CH:39][CH:38]=2)=[C:9]([C:31]2[CH:32]=[CH:33][C:34]([S:44]([Cl:43])(=[O:47])=[O:45])=[CH:35][CH:36]=2)[C:10]([C:25]2[CH:26]=[CH:27][C:28]([S:44]([Cl:43])(=[O:47])=[O:45])=[CH:29][CH:30]=2)=[C:11]([C:19]2[CH:24]=[CH:23][C:22]([S:44]([Cl:43])(=[O:47])=[O:45])=[CH:21][CH:20]=2)[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([S:44]([Cl:43])(=[O:47])=[O:45])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 86590332HCID 86590332, compound

Product 1

HCID 22558273HCID 22558273, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 mL round bottom flask was charged with 2.0 g (0.004 mol) of 1-hexyl-2,3,4,5,6-pentaphenylbenzene and 50 mL of dichloromethane. Chlorosulfonic acid (15 mL) was added to the stirred reaction mixture at room temperature via an addition funnel. The reaction mixture turned immediately purple, and then clear orange after 1 h. The reaction mixture was stirred at room temperature for 1 d, and then poured onto crushed ice. The layers were separated, and the aqueous layer was extracted twice with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated to deposit a light-gray solid. The product was recrystallized from ethyl acetate to provide 1.39 g (57%) of a white powder. 1H NMR (CDCl3) δ 7.96 (d, J=10, 4 H), 7.66 (m, 6), 7.41 (d, J=10, 4H), 7.08 (m, 6H). MS (FD) m/e 1034 (M+).

Workup

  1. additionpoured
  2. customonto crushed ice
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice with dichloromethane
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-36d57395ada74759bca89b10765cdf9e
Source dataset
uspto-grants-2004_02
Patent number
US06686407B2

Reaction notes

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