Hydrochloric Acid → HCID 12422794, compound

HRID 2398826Notes

Reaction equation

HRID 2398826 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH:16]([C:19]1[CH:27]=[CH:26][C:25]([CH3:28])=[C:21]([C:22]([OH:24])=[O:23])[C:20]=1[OH:29])([CH3:18])[CH3:17].Cl>[N+](C1C=CC=CC=1)([O-])=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:26]2[C:25]([CH3:28])=[C:21]([C:22]([OH:24])=[O:23])[C:20]([OH:29])=[C:19]([CH:16]([CH3:18])[CH3:17])[CH:27]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 11052o-Thymotic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12422794HCID 12422794, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

4-Chlorophenylsulphonyl chloride (6.3 g.) is added to a mixture of aluminium chloride (8.1 g.) and 3-isopropyl-6-methylsalicylic acid (5.7 g.) in dry nitrobenzene (3 ml.). The mixture is heated at 95°-100° C. for 4 hours and is then stirred into a mixture of ice (250 g.) and concentrated hydrochloric acid (30 ml.). The mixture is subsequently extracted with ethyl acetate (3 × 250 ml.). The extracts are washed with water and are then concentrated in vacuo. Residual nitrobenzene is removed by steam distillation. The oily solid, which remains after decantation of the water from the distillation residue, is crystallised from a mixture of xylene and petroleum ether (b.p. 60°-80° C.) to give 5-(4-chlorophenylsulphonyl)-3-isopropyl-6-methylsalicylic acid, m.p. 165°-166° C.

Workup

  1. temperatureThe mixture is heated at 95°-100° C. for 4 hours
  2. extractionThe mixture is subsequently extracted with ethyl acetate (3 × 250 ml.)
  3. washThe extracts are washed with water
  4. concentrationare then concentrated in vacuo
  5. customResidual nitrobenzene is removed by steam distillation
  6. customis crystallised from a mixture of xylene and petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-372031955876426fa24cba765a8a7df7
Source dataset
uspto-grants-1977_05
Patent number
US04025647

Reaction notes

Loading…