O-Xylene → HCID 86742248, compound

HRID 580617Notes

Reaction equation

HRID 580617 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=O)=[CH:5][C:4]=1[CH3:25].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].C1(C)C(C)=CC=CC=1>C1CCCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[S:27])=[CH:5][C:4]=1[CH3:25]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 14817Phosphorus sulfide (P2S5)HCID 54465264HCID 54465264, compound

Product 1

HCID 86742248HCID 86742248, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

6.75 g (20 mmols) of 3-(4-methoxy-3-methylphenyl)-3-phenylacrylic acid morpholide and 2.22 g (10 mmols) of finely ground phosphorus pentasulfide were refluxed unit 50 ml of absolute xylene for 3 horus. After cooling, the insoluble matter was filtered off, and the filtrate was washed with water, dried and concentrated by evaporation in vacuo. This concentrate was purified on a silica gel column. Elution was carried out first with toluene and then with a toluene/diisopropylether mixture in the proportions 90:10, then in the proportions 80:20. The fractions containing the substance with Rf 0.59 (toluene/diisopropylether 1:1) were concentrated by evaporation in vacuo, and the yellow oil obtained thereby was dissolved in cyclohexane, while heating. Upon cooling, the desired substance crystallized out.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insoluble matter was filtered off
  3. washthe filtrate was washed with water
  4. customdried
  5. concentrationconcentrated by evaporation in vacuo
  6. customThis concentrate was purified on a silica gel column
  7. washElution
  8. additionThe fractions containing the substance with Rf 0.59 (toluene/diisopropylether 1:1)
  9. concentrationwere concentrated by evaporation in vacuo
  10. customthe yellow oil obtained
  11. temperaturewhile heating
  12. temperatureUpon cooling
  13. customthe desired substance crystallized out

Sources & evidence

ORD record
ord-7d836e8b1c2541d3b64f517b8272666a
Source dataset
uspto-grants-1988_06
Patent number
US04753934

Reaction notes

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