p-Toluenesulfonic acid → 3-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzylidene] hydantoin

HRID 847722Notes

Reaction equation

HRID 847722 reaction equation
C1C(C=O)=CC=C(C=O)C=1.C(O)(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:26]1[CH:30]=[CH:29][O:28][CH:27]1[C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1.[CH2:39]([N:43]1[C:47](=[O:48])[CH2:46][NH:45][C:44]1=[O:49])[CH2:40][CH2:41][CH3:42]>C1C=CC=CC=1.O>[CH2:39]([N:43]1[C:47](=[O:48])[C:46](=[CH:35][C:34]2[CH:37]=[CH:38][C:31]([CH:27]3[O:28][CH:29]=[CH:30][O:26]3)=[CH:32][CH:33]=2)[NH:45][C:44]1=[O:49])[CH2:40][CH2:41][CH3:42]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 12173TerephthalaldehydeHCID 1512111,1-EthanediolHCID 5682353-Butylimidazolidine-2,4-dioneHCID 205672414-(1,3-Dioxol-2-yl)benzaldehyde

Product 1

HCID 540444323-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzylidene] hydantoin

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Terephthaldialdehyde (67 g; 0.5 mole), ethanediol (31 g, 0.5 mole) and p-toluenesulphonic acid (0.5 g) in benzene (400 ml.) were boiled under reflux for 2 hours, with the removal of the water formed via a Dean and Stark separator. After cooling, the mixture was washed with dilute sodium bicarbonate solution (100 ml, 2% W/V), then saturated sodium chloride solution (2×100 ml.) and dried over magnesium sulphate. After filtration, the benzene solution was evaporated in vacuo to give a straw-coloured oil containing ca 70% of the desired aldehyde, viz: 4-(1,3-dioxol-2-yl)benzaldehyde, which was reacted with 3-n-butylhydantoin as in Example 1.

Workup

  1. customformed via a Dean and Stark separator
  2. temperatureAfter cooling
  3. washthe mixture was washed with dilute sodium bicarbonate solution (100 ml, 2% W/V)
  4. dry with materialsaturated sodium chloride solution (2×100 ml.) and dried over magnesium sulphate
  5. filtrationAfter filtration
  6. customthe benzene solution was evaporated in vacuo
  7. customto give a straw-coloured oil

Sources & evidence

ORD record
ord-dade0a8c3ac044bca261fa2a3dd18b61
Source dataset
uspto-grants-1981_10
Patent number
US04293563

Reaction notes

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