Hydrochloric Acid → STK367740

HRID 1614438Notes

Reaction equation

HRID 1614438 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 (1.2M, 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) v: 3089, 3066, 3033, 2900, 1692(C=O), 1676, 1568, 1492, 1454, 1404, 1325, 1309, 1272, 1217, 1202 cm-1H NMR (200 MHz, CDCl3) δ: 4.30 (s, 4H, --CH2Ph), 7.24-7.37 (m, 10H, ending phenyls), 8.06 (s, 4H, phenylene). MS [m/e (70 eV, % 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-67d0ce4031ef4639be977e19db671160
Source dataset
uspto-grants-1993_03
Patent number
US05196606

Reaction notes

Loading…