p-Toluenesulfonic acid → HCID 12816480, compound

HRID 2059039Notes

Reaction equation

HRID 2059039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:17])[CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[CH3:18][C:19]([CH3:24])([CH2:22]O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH2:11][N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[O:21][CH2:20][C:19]([CH3:24])([CH3:22])[CH2:18][O:17]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 31344Neopentyl glycolHCID 110103354-(4-Chlorophenyl)-1-(imidazol-1-yl)butan-2-one

Product 1

HCID 12816480HCID 12816480, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-[4-(4-chlorophenyl)butan-2-on-1-yl]imidazole (2.0 g), 2,2-dimethylpropane-1,3-diol (0.84 g) and anhydrous p-toluenesulfonic acid (1.39 g) in toluene (20 ml) were heated under reflux through a Dean-Stark trap for 2 hours. The resulting mixture was poured into aqueous potassium carbonate solution, extracted with ether (2×100 ml) and the extracts dried (MgSO4). After removal of the solvent, the crude reaction product was chromatographed on silica gel eluting with 7% methanol in methylene chloride to give 1-[[2-(2-(4-chlorophenyl)ethyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl]imidazole (1.0 g) as a colorless oil which crystallized. The oil was dissolved in ether, the solution filtered and the hydrochloride salt formed by dropwise addition of ethereal hydrogen chloride until precipitation was almost complete. The precipitate was filtered, washed with ether and dried in vacuo to give 1-[[2-(2-(4-chlorophenyl)ethyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl]imidazole hydrochloride, m.p. 190°-191° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux through a Dean-Stark trap for 2 hours
  3. extractionextracted with ether (2×100 ml)
  4. dry with materialthe extracts dried (MgSO4)
  5. customAfter removal of the solvent
  6. customthe crude reaction product
  7. customwas chromatographed on silica gel eluting with 7% methanol in methylene chloride

Sources & evidence

ORD record
ord-1dca1e16ce4944deb090a73ba35bda40
Source dataset
uspto-grants-1982_03
Patent number
US04321272

Reaction notes

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