p-Toluenesulfonic acid → HCID 20239914, compound

HRID 363991Notes

Reaction equation

HRID 363991 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH:11]([C:15](=[O:18])[CH2:16][CH3:17])[C:10](=[O:19])[CH:9]1[C:20]([O:22]CC)=[O:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:15]([CH:11]1[C:12](=[O:14])[CH2:13][CH:8]2[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:22][C:20](=[O:21])[CH:9]2[C:10]1=[O:19])(=[O:18])[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20239930HCID 20239930, compound

Product 1

HCID 20239914HCID 20239914, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(2-hydroxyphenyl)-4-ethoxycarbonyl-2-propionylcyclohexane-1,3-dione (100 mg) and p-toluenesulphonic acid (10 mg) in toluene (5 ml) was heated under reflux for 1 hour. The solution was washed with dilute aqueous sodium bicarbonate and the toluene layer was dried (MgSO4) and evaporated to give 8-propionyl-10,10a-dihydro-6H-dibenzo[b,d]-pyran-6,7,9-(6aH,8H)trione (80 mg) as a pale yellow oil, proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 0.8-1.3 (3H,m); 2.8-4.0 (6H,m); 6.9 (4H,bs); 18.1 (1H,bs).

Workup

  1. temperatureunder reflux for 1 hour
  2. washThe solution was washed with dilute aqueous sodium bicarbonate
  3. dry with materialthe toluene layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-2808ccd2f1774d2fb35c1d2f72716219
Source dataset
uspto-grants-1986_08
Patent number
US04604128

Reaction notes

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