Adipic Acid → Divinyl adipate

HRID 249457Notes

Reaction equation

HRID 249457 reaction equation
[C:1]([O:4][CH:5]=[CH2:6])(=[O:3])[CH3:2].C(O)(=O)C[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[C:17]1(C)C=CC(S(O)(=O)=O)=C[CH:18]=1.CC([O-])=O.[Na+]>>[C:12]([O:14][CH:17]=[CH2:18])(=[O:13])[CH2:11][CH2:10][CH2:9][CH2:2][C:1]([O:4][CH:5]=[CH2:6])=[O:3]

Participants

5

Reactant 4

HCID 196Adipic AcidHCID 6101p-Toluenesulfonic acidHCID 7904Vinyl AcetateHCID 517045Sodium Acetate

Product 1

HCID 19997Divinyl adipateYield 99.7%

Procedure

In a 3-necked 1000 ml round bottom flask equipped with a reflux condenser, thermometer and magnetic stirrer was added vinyl acetate (320 g, 3791 mmol), adipic acid (17.5 g, 120 mmol), [pyridine]2Pd(OAc)2 (1.2 g, 3.1 mmol) and p-toluenesulfonic acid (4.4 g, 25.6 mmol). The temperature was held at 65° C. for 4 hours. After cooling to room temperature, NaOAc (3.0 g) was added to the solution. Volatiles were removed by a roto-vac. The non-volatiles were diluted with 200 ml hexane, extracted with 2×100 ml 2% NaOH, extracted with 100 ml distilled water and then dried over Na2SO4. The hexane was removed with a roto-vac. TLC showed on component. The divinyl adipate weighed 23.7 g (99.7% yield). IR(NaCl plate): 2940, 1750, 1640, 1370 cm-1.

Workup

  1. customIn a 3-necked 1000 ml round bottom flask equipped with a reflux condenser
  2. customVolatiles were removed by a roto-vac
  3. additionThe non-volatiles were diluted with 200 ml hexane
  4. extractionextracted with 2×100 ml 2% NaOH
  5. extractionextracted with 100 ml
  6. distillationdistilled water
  7. dry with materialdried over Na2SO4
  8. customThe hexane was removed with a roto-vac

Sources & evidence

ORD record
ord-5ef38c2c2a894e718f33c3356e7c49ee
Source dataset
uspto-grants-1993_05
Patent number
US05214172

Reaction notes

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