p-Toluenesulfonic acid → HCID 18977980, compound

HRID 2393038Notes

Reaction equation

HRID 2393038 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:3]=1[C:4]([CH:6]([C:14](=[O:17])[CH2:15][CH3:16])C(OC(C)(C)C)=O)=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[C:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:19]=[CH:18][C:3]=1[C:4](=[O:5])[CH2:6][C:14](=[O:17])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18978032HCID 18978032, compound

Product 1

HCID 18977980HCID 18977980, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of crude t-butyl 2-[2-chloro-4-(methylsulphonyl)benzoyl]-3-oxopentanoate (12.0 g) and 4-toluenesulphonic acid (0.1 g) in toluene was stirred and heated at reflux for 3.5 hours. After cooling, the mixture was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ether and filtered to give 1-[2-chloro-4-(methylsulphonyl)phenyl]pentan-1,3-dione (7.02 g) as a white solid NMR(CDCl3): 1.2(t,3H) 2.45 (q,2H) 3.0(s,3H) 5.9(s,1H) 7.5-8.0(m,3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 hours
  3. temperatureAfter cooling
  4. washthe mixture was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was triturated with ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-9e90ab336c704b259b011edd284ef300
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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