Chlorosulfonic acid → HCID 19854187, compound

HRID 1649631Notes

Reaction equation

HRID 1649631 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[OH:6][C:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:11][CH2:10][C:9](=[O:20])[C:8]=1[C:21](=[O:24])[CH2:22][CH3:23]>C(Cl)(Cl)Cl>[OH:6][C:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:14]=2)[CH2:11][CH2:10][C:9](=[O:20])[C:8]=1[C:21](=[O:24])[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 19854198HCID 19854198, compound

Product 1

HCID 19854187HCID 19854187, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Chlorosulphonic acid (20 ml) was added dropwise to an ice-cold solution of 3-hydroxy-2-propionyl-4-(4-methylphenyl)cyclohex-2-ene-1-one (3.25 g) in chloroform (40 ml). After stirring at room temperature for 4 hours, the mixture was carefully poured onto ice. The chloroform layer was separated and the aqueous phase extracted with more chloroform. The combined extracts were dried over magnesium sulphate, filtered and the chloroform evaporated in vacuo to give 3-hydroxy-2-propionyl-4-(3-chlorosulphonyl-4-methylphenyl)cyclohex-2-ene-1-one (4.4 g). Water (50 ml) was added to the latter, followed by dimethylamine (2 g) and the solution stirred at room temperature for 1/2 hour. The solution was acidified with dilute hydrochloric acid, and extracted with dichloromethane. After drying over magnesium sulphate, the dichloromethane was evaporated in vacuo to give a pale yellow oil. Purification on a silica gel column using chloroform as eluant gave the title compound (4.0 g) as a white solid of m.p. 95°-97° C.

Workup

  1. additionthe mixture was carefully poured onto ice
  2. customThe chloroform layer was separated
  3. extractionthe aqueous phase extracted with more chloroform
  4. dry with materialThe combined extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe chloroform evaporated in vacuo

Sources & evidence

ORD record
ord-80ae5a4a181f4706ab5ceb2954de84a6
Source dataset
uspto-grants-1990_05
Patent number
US04921524

Reaction notes

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