Acetic Anhydride → Phenylitaconic anhydride

HRID 1109626Notes

Reaction equation

HRID 1109626 reaction equation
C(OC(=O)C)(=O)C.[C:8]1(/[CH:14]=[C:15](\[CH2:19][C:20]([OH:22])=[O:21])/[C:16]([OH:18])=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[C:8]1([CH:14]=[C:15]2[CH2:19][C:20](=[O:21])[O:22][C:16]2=[O:18])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 820629(2E)-2-Benzylidenebutanedioic Acid

Product 1

HCID 222996Phenylitaconic anhydride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.3 l (approx. 2.49 kg, approx. 24.4 mol) of acetic anhydride are added at 20° C. to a solution of 2.28 kg (11.1 mol) of (E)-phenylitaconic acid in 5.7 l of THF. The mixture is stirred for 5 hours at room temperature. After 1 hour there is a clear light yellow solution; after 3 hours the product begins to crystallize out. The THF is removed under vacuum, 5.0 l of methyl tert-butyl ether are added to the residue in order to complete the crystallization, and the product is filtered off with suction. It is washed with MTB ether, dried with suction and dried under vacuum at 40° C. Yield: 1.68 kg (8.94 mol, 81% of theory), m.p. 167°-170° C.

Workup

  1. waitAfter 1 hour there is
  2. waitafter 3 hours the product begins
  3. customto crystallize out
  4. customThe THF is removed under vacuum, 5.0 l of methyl tert-butyl ether
  5. additionare added to the residue in order
  6. customthe crystallization
  7. filtrationthe product is filtered off with suction
  8. washIt is washed with MTB ether
  9. customdried with suction
  10. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-893e78c5c79b454bb4ac749c2a386de9
Source dataset
uspto-grants-1994_06
Patent number
US05321139

Reaction notes

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