Water → 2-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane

HRID 2229271Notes

Reaction equation

HRID 2229271 reaction equation
[C:1]1([CH3:7])C=CC=CC=1.O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:17])=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=[O:34])=CC=1>C(O)CO>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[O:34][CH2:1][CH2:7][O:17]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 3477714-Chloro-4'-nitrobenzophenone

Product 1

HCID 154896262-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolaneYield 91%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Toluene (1900 ml) was stirred in a round-bottom flask (5 l) using a water separator. (4-Chlorophenyl)(4-nitrophenyl)methanone (250 g) was added portionwise. p-Toluene-sulfonic acid (54.5 g) was added portionwise. Ethylene glycol (237.5 g) was poured out into the mixture. The mixture was stirred and refluxed for 48 hours. The solvent was evaporated. The residue was dissolved into ethyl acetate (5 l) and washed twice with a K2CO3 10% solution. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was stirred in DIPE, filtered off and dried (vacuum, 40° C., 24 hours), yielding 265 g (91%) of 2-(4-chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane (interm. 5-a).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved into ethyl acetate (5 l)
  4. washwashed twice with a K2CO3 10% solution
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. stirringThe residue was stirred in DIPE
  10. filtrationfiltered off
  11. customdried (vacuum, 40° C., 24 hours)

Sources & evidence

ORD record
ord-38ffd1be0d384c2f97294dacfe06b55e
Source dataset
uspto-grants-2002_07
Patent number
US06420387B1

Reaction notes

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