Isobutyric anhydride → Methylene bisisobutyrate

HRID 1579850Notes

Reaction equation

HRID 1579850 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4]OO1.[C:7]([O:12][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])(=[O:11])C(C)C.Cl(O)(=O)(=O)=O.[C:23](=O)(O)[O-].[Na+]>>[C:13]([O:12][CH2:7][O:11][C:6](=[O:1])[CH:5]([CH3:23])[CH3:4])(=[O:17])[CH:14]([CH3:15])[CH3:16]

Participants

5

Reactant 4

HCID 7346Isobutyric anhydrideHCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 19593658CID 19593658

Product 1

HCID 12851389Methylene bisisobutyrate

Procedure

A 30-g (0.33 mol) sample of trioxane was added to a solution of 158 g (1 mol) isobutyric anhydride and 0.5 ml 70 percent perchloric acid over a 30-minute period at 65°-70°C. The reaction mixture was then stirred until the temperature decreased to 27°C. The reaction mixture was diluted with saturated sodium bicarbonate solution and extracted with ether. The ether extracts were dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was distilled on a 30-cm column to give 112 g of methylene bisisobutyrate, b.p. 43°-48°C. at 0.2-0.3 mm of Hg and 30 g of oxybismethylene isobutyrate, b.p. 57°-63°C. at 0.2-0.3 mm of Hg.

Workup

  1. customdecreased to 27°C
  2. extractionextracted with ether
  3. dry with materialThe ether extracts were dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. distillationThe resulting residue was distilled on a 30-cm column

Sources & evidence

ORD record
ord-2935779b255b49498ab1f3960a3a4785
Source dataset
uspto-grants-1976_01
Patent number
US03931412

Reaction notes

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