p-Toluenesulfonic acid → HCID 10421644, compound

HRID 1735825Notes

Reaction equation

HRID 1735825 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:14])[CH2:9][CH2:10][C:11](=O)[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:12][C:11]1[O:14][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10060908HCID 10060908, compound

Product 1

HCID 10421644HCID 10421644, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 18 g of 1-(2-bromophenyl)-1,4-pentanedione and 1 g of p-toluenesulfonic acid in 200 ml of anhydrous benzene is heated under reflux over molecular sieves for 12 h. The resulting solution is washed 3 times with brine, dried over Na2SO4 and evaporated to dryness under reduced pressure. The residue is purified by FC (eluent hexane:acetate 95:5) and 12.2 of a light yellow oil are obtained g (70% yield). 1H NMR (CDCl3), δ: 2.38 (d, 3 H), 6.12 (m, 1 H), 7.1-7.4 (m, 3 H), 7.63 (dd, 1 H), 7.79 (dd, 1 H).

Workup

  1. temperatureunder reflux over molecular sieves for 12 h
  2. washThe resulting solution is washed 3 times with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is purified by FC (eluent hexane:acetate 95:5) and 12.2 of a light yellow oil
  6. customare obtained

Sources & evidence

ORD record
ord-957969dfc5394688b6633ee8920087c6
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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