p-Toluenesulfonic acid → HCID 21569624, compound

HRID 1579863Notes

Reaction equation

HRID 1579863 reaction equation
[CH2:1]([CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[NH2:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([O:28][CH2:29][P:30]([CH3:33])([CH3:32])=[O:31])=[O:27])=[CH:24][CH:23]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:33][P:30]([CH2:29][O:28][C:26]([C:25]1[CH:24]=[CH:23][C:22]([N:21]2[C:11]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[CH2:18][CH2:19][C:10]=3[CH:1]=[C:2]2[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:35][CH:34]=1)=[O:27])([CH3:32])=[O:31]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 122703462-phenacyl-1-tetraloneHCID 21569607HCID 21569607, compound

Product 1

HCID 21569624HCID 21569624, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.6 g. (0.01 mole) of 2-phenacyl-1-tetralone, 2.3 g. (0.01 mole) of dimethylphosphinylmethyl p-aminobenzoate, 0.4 g. of p-toluenesulfonic acid, and 250 ml. of dry toluene was heated under reflux for 73 hours, concentrated to about 100 ml., diluted with 25 ml. of cyclohexane, and cooled. The solid which separated was collected to provide 2.6 g. (57%) of solid, m.p. 171°-173°. Recrystallization from cyclohexane-benzene gave pale yellow crystals, m.p. 180°-181°.

Workup

  1. additionA mixture of 2.6 g
  2. temperatureunder reflux for 73 hours
  3. concentrationconcentrated to about 100 ml
  4. addition, diluted with 25 ml
  5. temperatureof cyclohexane, and cooled
  6. customThe solid which separated
  7. customwas collected
  8. customto provide 2.6 g
  9. customRecrystallization from cyclohexane-benzene
  10. customgave pale yellow crystals, m.p. 180°-181°

Sources & evidence

ORD record
ord-62502f782efd4959b2f2966e1003eaec
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

Loading…