p-Toluenesulfonic acid → 2-Methyl-2-(4-nitrophenyl)-1,3-dioxolane

HRID 1380006Notes

Reaction equation

HRID 1380006 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].C(OCC)(OCC)[O:14][CH2:15][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C(Cl)Cl.C(O)CO>[CH3:1][C:2]1([C:4]2[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=2)[O:14][CH2:15][CH2:16][O:3]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7487p-NitroacetophenoneHCID 14798Sodium HydroxideHCID 31214Ethyl orthoformate

Product 1

HCID 6065982-Methyl-2-(4-nitrophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 6344DichloromethaneSolvent

Procedure

P-Nitroacetophenone (1.65 g, 10 m mol), ethylene glycol (5 ml, 89 m mol), triethyl orthoformate (2.96 g, 20 m mol), and p-toluenesulfonic acid (0.086 g, 0.5 m mol) were combined in methylene chloride (4 ml). The solution was heated with an oil bath (50°-70° C., 6 hrs), cooled to room temperature, and poured into excess 10% sodium hydroxide solution. The phases were separated and the aqueous phase was extracted twice with methylene chloride. The combined organic phase was washed three times with water and dried with anhydrous sodium sulphate. Evaporation of the solvent left a light yellow product (1.78 g) with mp. 69°-71° C., (lit. 73°-75° C., see J. Pharm. Sci. 57, 784 (1968)).

Workup

  1. temperatureThe solution was heated with an oil bath (50°-70° C., 6 hrs)
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with methylene chloride
  4. washThe combined organic phase was washed three times with water
  5. dry with materialdried with anhydrous sodium sulphate
  6. customEvaporation of the solvent
  7. waitleft a light yellow product (1.78 g) with mp. 69°-71° C., (lit. 73°-75° C., see J. Pharm. Sci. 57, 784 (1968))

Sources & evidence

ORD record
ord-63c671eb759f436fbbe69c307c68d7b5
Source dataset
uspto-grants-1986_04
Patent number
US04579679

Reaction notes

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