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Chlorosulfonic acid → 2,4,6-Trimethoxybenzene-1-sulfonyl chloride

HRID 1164284
Notes
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Reaction equation

HRID 1164284 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[CH:4]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>ClCCl>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[C:6]=1[S:14]([Cl:13])(=[O:16])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 693011,3,5-Trimethoxybenzene

Product 1

HCID 159175192,4,6-Trimethoxybenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 500 ml of dichloromethane is dissolved 5.05 g of 1,3,5-trimethoxybenzene and the solution was cooled to -5°~-10° C. A solution of 6 ml of chlorosulfonic acid in 400 ml of dichloromethane was added dropwise, and the mixture was allowed to stand at room temperature. The reaction mixture was then treated as in Reference Example 1. The resulting product was crystallized from carbon tetrachloride and filtered. Yield 610 mg (6.3%), m.p. 126°-129° C.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. temperaturethe solution was cooled to -5°~-10° C
  2. customto stand at room temperature
  3. additionThe reaction mixture was then treated as in Reference Example 1
  4. customThe resulting product was crystallized from carbon tetrachloride
  5. filtrationfiltered

Sources & evidence

ORD record
ord-97908d4f72fc4d4e9c1d12f421265b35
Source dataset
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04368150

Reaction notes

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