Azobisisobutyronitrile → HCID 178459095, compound

HRID 1972299

Reaction equation

HRID 1972299 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.C[CH2:14][C:15]([CH2:20][O:21][CH2:22][CH:23]=[CH2:24])(CO)CO.[C:25]([OH:30])(=[S:29])[CH:26]([CH3:28])[OH:27]>CO.C1(C)C=CC=CC=1.CCCCCC>[CH2:20]([O:21][CH2:22][CH:23]=[CH2:24])[CH:15]=[CH2:14].[C:25]([OH:30])(=[S:29])[CH:26]([CH3:28])[OH:27]

Participants

7

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 12683Trimethylolpropane monoallyl etherHCID 178473673HCID 178473673, compound

Product 1

HCID 178459095HCID 178459095, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

AIBN (1.5 g) was dissolved in trimethylolpropane monoallyl ether (497 g, 2.86 mol). This solution was slowly added, under nitrogen with stirring, to thiolactic acid (300 g, 2.83 mol) at such a rate that the temperature of the exothermal reaction was kept at 80° C. When the addition was completed, the temperature was raised to 90° C. and kept at 90° C. for 1 h. The product had 1H-NMR (CDCl3): δ 1.11 (t, 3H, CH3CH2), 1.53 (q, 2H, CH3CH2), 2.00-2.20 (m, 2H, CH2CH2CH2), 2.98-3.06 (m, 2H, 3.65-4.02 (m, 9H); and is soluble in methanol and toluene, not soluble in hexane.

Workup

  1. additionThis solution was slowly added, under nitrogen
  2. customthat the temperature of the exothermal reaction
  3. customwas kept at 80° C
  4. additionWhen the addition

Sources & evidence

ORD record
ord-641a1f01701d42dc9ace8d49418ea828
Source dataset
uspto-grants-2013_04
Patent number
US08431748B2

Linked notes

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