Toluene → Ethanol ethylacetate

HRID 1728314Notes

Reaction equation

HRID 1728314 reaction equation
[C:1]1(=[O:6])[CH2:5]CC[CH2:2]1.C1(C)C=CC(S(O)(=O)=[O:14])=CC=1.[C:18]1([CH3:24])C=CC=CC=1>>[C:18]([O:6][CH2:1][CH3:5])(=[O:14])[CH3:24].[CH2:1]([OH:6])[CH3:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 8452Cyclopentanone

Product 1

HCID 21584252Ethanol ethylacetateYield 39%

Conditions

Temperature
55 °C

Procedure

2-Amino-4,5-dimethoxyacetophanone oxime (1.0 g, 4.76 mmol) was suspended in 35 ml toluene, and cyclopentanone (0.42 ml, 4.76 mmol) was added, followed by 10 mg of p- toluenesulfonic acid. The mixture was stirred at 55° C. for 24 hours. The resultant solid was collected by filtration and recrystallized from ethyl acetate-ethanol (39% yield). m.p. 225°-227 C.

Workup

  1. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-2de7a848a79b43f5adb57729eb50c425
Source dataset
uspto-grants-1994_07
Patent number
US05326765

Reaction notes

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