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

HRID 852268Notes

Reaction equation

HRID 852268 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 K2CO310% solution. The organic layer was separated, dried, 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 K2CO310% solution
  5. customThe organic layer was separated
  6. customdried
  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-c7c21cff424b4c23857020e3cb0b3d05
Source dataset
uspto-grants-2007_08
Patent number
US07253183B2

Reaction notes

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