Chlorosulfonic acid → HCID 178450335, compound

HRID 235600Notes

Reaction equation

HRID 235600 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([C:11]1[C:12](=[O:28])[CH2:13][CH:14]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH2:15][C:16]=1[OH:17])(=[O:10])[CH2:7][CH2:8][CH3:9]>C(Cl)(Cl)Cl>[C:6]([C:11]1[C:16](=[O:17])[CH2:15][CH:14]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:20][CH:19]=2)[CH2:13][C:12]=1[OH:28])(=[O:10])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178450308HCID 178450308, compound

Product 1

HCID 178450335HCID 178450335, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (3.0 g) was added dropwise to a solution of 2-butyryl-3-hydroxy-5-(naphth-1-yl)cyclohex-2-en-1-one (1.3 g) in chloroform (15 ml) at 0° C. The mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hrs. The mixture was poured onto ice-water (200 ml) which was subsequently extracted with dichloromethane. The dried (Na2SO4) organic extract was evaporated to give 2-butyryl-5-(4-chlorosulfonylnaphth-1-yl)-3-hydroxy cyclohex-2-en-1-one as a brown foam. Pmr spectrum (CDCl3 ; δ in ppm): 1.03 (3H,t); 1.43-1.89 (2H,m); 2.69-3.26 (6H,m); 4.00-4.49 (1H,m); 7.32-8.97 (6H,m); 18.35 (1H,s).

Workup

  1. additionThe mixture was poured onto ice-water (200 ml) which
  2. extractionwas subsequently extracted with dichloromethane
  3. dry with materialThe dried (Na2SO4)
  4. extractionorganic extract
  5. customwas evaporated

Sources & evidence

ORD record
ord-1e569987420f4d80bd50eb90fdf87bed
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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