p-Toluenesulfonic acid → 3-n-Butyl-5-(4-formylbenzyl) hydantoin

HRID 1733310Notes

Reaction equation

HRID 1733310 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3OC=C[O:19]3)=[CH:14][CH:13]=2)[NH:7][C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]=[O:19])=[CH:16][CH:17]=2)[NH:7][C:6]1=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 705497123-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzyl] hydantoin

Product 1

HCID 127907213-n-Butyl-5-(4-formylbenzyl) hydantoin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzyl] hydantoin (5.5 g., 0.017 mole) was dissolved in acetone (150 ml.) and stirred overnight at room temperature with p-toluene sulphonic acid (0.5 g). The acetone was evaporated off in vacuo and the residual oily solid partitioned between water and chloroform. The chloroform phase was washed with sodium carbonate solution (2% W/V), then evaporated in vacuo to give a yellow oil which slowly crystallised and was recrystallised from petroleum ether 60°/80° C./ethyl acetate (3/1 V/V) to give 3-n-butyl-5-(4-formylbenzyl) hydantoin, 4.5 g (95%), m.p. 160° C.

Workup

  1. customThe acetone was evaporated off in vacuo
  2. customthe residual oily solid partitioned between water and chloroform
  3. washThe chloroform phase was washed with sodium carbonate solution (2% W/V)
  4. customevaporated in vacuo
  5. customto give a yellow oil which
  6. customslowly crystallised
  7. customwas recrystallised from petroleum ether 60°/80° C./ethyl acetate (3/1 V/V)

Sources & evidence

ORD record
ord-b262b8b4baf54b10973d5b0f984725fd
Source dataset
uspto-grants-1980_12
Patent number
US04241073

Reaction notes

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