Hydrochloric Acid → STK367740

HRID 1197246Notes

Reaction equation

HRID 1197246 reaction equation
Cl.[C:2]1([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[C:5]1([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:2]([C:8](=[O:16])[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 99482-Phenylacetophenone

Product 1

HCID 3844928STK367740

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chromatographed (E),(E)-1,1'-[1,4-phenylene]bis[2-phenyl-1-(diphenylamino)ethylene](1.0 g, 0.0016 mol) was refluxed in a solution of THF (30 mL) and aqueous HCl (1.2 M, 3.0 mL) for 1.25 h. The solution was worked-up as for the preparation of 1,2-diphenylethanone. Chromatography on silica (30 g) eluting with petroleum ether/benzene 3:2 removed the diketone. After solvent evaporation of the combined fractions and recrystallization of the residue from benzene/methanol gave small plates mp 171°-3° C. (85%). FTIR (CDCl3)ν: 3089, 3066, 3033, 2900, 1592(C=O), 1676, 1568, 1492, 1454, 1404, 1325, 1309, 1272, 1217, 1202 cm-1. 1H NMR (200 MHz, CDCl3)δ4.30(s, 4H, --CH2Ph), 7.24-7.37(m, 10 H, ending phenyls), 8.06(s,4 H, phenylene).MS [m/e(70eV,% of base peak)]C22H18O2 314(M+·, 0.8), 223(M+ · --PhCH2·, 100), 104(C6H4CO+, 42.9), 91(C7H7+, 29).

Workup

  1. washChromatography on silica (30 g) eluting with petroleum ether/benzene 3:2
  2. customremoved the diketone
  3. customAfter solvent evaporation of the combined fractions and recrystallization of the residue from benzene/methanol
  4. customgave small plates mp 171°-3° C. (85%)

Sources & evidence

ORD record
ord-953be78e3d2048d4bfdb5947f3d148d6
Source dataset
uspto-grants-1992_05
Patent number
US05117062

Reaction notes

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