Chlorosulfonic acid → HCID 178458884, compound

HRID 1583887Notes

Reaction equation

HRID 1583887 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[OH:6][C:7]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[CH2:10][C:9](=[O:21])[C:8]=1[C:22](=[O:25])[CH2:23][CH3:24]>C(Cl)(Cl)Cl>[OH:6][C:7]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[C:15]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:14]=2)[CH2:10][C:9](=[O:21])[C:8]=1[C:22](=[O:25])[CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178458883HCID 178458883, compound

Product 1

HCID 178458884HCID 178458884, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(i) Chlorosulfonic acid (9.5 ml) was added dropwise to a solution of 3-hydroxy-5-[4-(methylthio)-phenyl]-2-propionylcyclohex-2-en-1-one (2.4 g) in chloroform (18 ml) at 0° C. After 15 hr, the solution was warmed to ambient temperature and after a further 3 hr the mixture was poured onto ice. The resulting mixture was extracted with dichloromethane and the organic extract was washed with water. Evaporation of the solvent gave 3-hydroxy-5-[3-chlorosulfonyl-4-(methylthio)phenyl]-2-propionylcyclohex-2-en-1-one (2.42 g). Pmr spectrum (CDCl3 ; δ in ppm): 1.14 (3H, t); 2.61 (3H, t); c.a. 2.6-3.68 (7H, m); 7.39-7.70 (2H, m); 7.94 (1H, s); 18.20 (1H, s).

Workup

  1. additionwas poured onto ice
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. extractionthe organic extract
  4. washwas washed with water
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-24974c89aba34f6bb89e2f0aac5b4f81
Source dataset
uspto-grants-1985_11
Patent number
US04555263

Reaction notes

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