Chlorosulfonic acid → HCID 178458849, compound

HRID 978979Notes

Reaction equation

HRID 978979 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[CH3:16])[CH2:5][C:4](=[O:17])[C:3]=1[C:18](=[O:21])[CH2:19][CH3:20].[Cl:22][S:23](O)(=[O:25])=[O:24]>C(Cl)(Cl)Cl>[OH:17][C:4]1[CH2:5][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([S:23]([Cl:22])(=[O:25])=[O:24])[C:9]=2[CH3:16])[CH2:7][C:2](=[O:1])[C:3]=1[C:18](=[O:21])[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178458835HCID 178458835, compound

Product 1

HCID 178458849HCID 178458849, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-hydroxy-5-mesityl-2-propionylcyclohex-2-en-1-one (1.8 g) in chloroform (20 ml) was stirred and cooled to 0° C. during the dropwise addition of chlorosulphonic acid (10 ml). The mixture was stirred for four hours at 20° C. and then poured into ice-water and the aqueous phase was extracted with chloroform (50 ml). The organic phase was dried over anhydrous sodium sulphate and the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The product 3-hydroxy-5-(2,4,6-trimethyl-3-chlorosulphonylphenyl)-2-propionylcyclohex-2-en-1-one was isolated as a brown oil (2.4 g, 97%). Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.16 (3H, t); 2.47 (3H, s); 2.69 (3H, s); 2.80 (3H, s); 2.7-4.0 (7H, m); 7.05 (1H, s); 18.30 (1H, s).

Workup

  1. extractionthe aqueous phase was extracted with chloroform (50 ml)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-3daa0c81d5e94e48aaae9a0581192db2
Source dataset
uspto-grants-1987_05
Patent number
US04666510

Reaction notes

Loading…