Azobisisobutyronitrile → 2-Ethylhexyl 2-(2-(2-oxo-1,3-dioxolan-4-yl)ethylthio)acetate

HRID 1486228Notes

Reaction equation

HRID 1486228 reaction equation
[CH:1]([CH:3]1[CH2:7][O:6][C:5](=[O:8])[O:4]1)=[CH2:2].[C:9]([O:13][CH2:14][CH:15]([CH2:20][CH3:21])[CH2:16][CH2:17][CH2:18][CH3:19])(=[O:12])[CH2:10][SH:11].N(C(C)(C)C#N)=NC(C)(C)C#N>>[O:8]=[C:5]1[O:4][CH:3]([CH2:1][CH2:2][S:11][CH2:10][C:9]([O:13][CH2:14][CH:15]([CH2:20][CH3:21])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:12])[CH2:7][O:6]1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 243092-Ethylhexyl thioglycolateHCID 27350381,3-Dioxolan-2-one, 4-ethenyl-

Product 1

HCID 1183895082-Ethylhexyl 2-(2-(2-oxo-1,3-dioxolan-4-yl)ethylthio)acetate

Conditions

Temperature
110 °C

Procedure

3.07 grams (26.9 mmol, MW: 114.10) 4-vinyl-1,3-dioxaolane-2-one, 5.0 grams (24.5 mmol, MW: 204.13) 2-ethylhexyl thioglycolate and 0.402 grams (2.45 mmol, MW: 164.21) 2,2′-azobis(2-methylpropionitrile) (AIBN) were charged in 25 milliliter thick sealed glass reactor. After addition, the reaction mixture was stirred for 22 hours at 110° C. The reaction was then stopped and cooled down to room temperature. The excess of unreacted 4-vinyl-1,3-dioxaolane-2-one was removed by air bath oven at 180° C. under vacuum for 1 hour. The final product was determined by IR, 13C NMR. Yield: 6.0 grams (77%). IR: (cm−1) 3046, 2957, 2926, 2870, 2857, 1596, 1510, 1458, 1394, 1378, 1260, 1219, 1165, 1077, 1016, 779, 730. 13C NMR (CDCl3): 170.4, 154.7, 75.5, 69.2, 67.8, 38.4, 33.7, 33.5, 30.3, 28.9, 27.8, 23.6, 22.9, 14.3, 10.7.

Workup

  1. customthick sealed glass reactor
  2. additionAfter addition
  3. temperaturecooled down to room temperature
  4. customThe excess of unreacted 4-vinyl-1,3-dioxaolane-2-one was removed by air bath oven at 180° C. under vacuum for 1 hour

Sources & evidence

ORD record
ord-08ed1549e52243e3bcfcf9ad2ec553cd
Source dataset
uspto-grants-2016_08
Patent number
US09422502B2

Reaction notes

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