Acetic Anhydride → HCID 3069818, compound

HRID 1578994Notes

Reaction equation

HRID 1578994 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[O:3].[CH3:14][C:15]([O:17]C(C)=O)=[O:16]>CCN(CC)CC>[F:13][C:10]([F:11])([F:12])[C:7]1[CH:8]=[CH:9][C:4]([C:2]([CH:1]=[CH:14][C:15]([OH:17])=[O:16])=[O:3])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-one

Product 1

HCID 3069818HCID 3069818, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

Freshly fused ZnCl2 (82 g, 0.6 mole) was dissolved in dry Et2O (400 ml) and added dropwise to the Grignard reagent prepared from 4-bromobenzotrifluoride (112.5g, 0.5 mole) and Mg (12.2 g, 0.5 g-atom) in Et2O (600 ml). Maleic anhydride (44 g, 0.45 mole) in Et2O (400 ml) was added over 30 minutes with stirring at reflux. After 2 hours, the mixture was cooled and acidified to pH 2 with 10% HCl. The Et2O layer was separated and dried (MgSO4), and the Et2O evaporated. The residue was recrystallized from C6H6 (x3) to yield the title compound, 24.5 g (21%), mp 149°-151°. Anal. (C11H7F3O3) C, H, F. An alternative procedure is as follows. A mixture of 4-trifluoromethylacetophenone (18.8 g) glyoxylic acid monohydrate (18.8 g), Ac2O(20 ml) and a drop of Et3N was heated to 135°, internal temperature. More Et3N (2 ml) was added, and the mixture was held at 135° for 20 minutes. The mixture was cooled and evaporated to dryness in vacuo. The solid residue was digested with H2O, filtered, dried and recrystallized from C6H6 to give the title compound, 12.2 g (50%), mp 149°-151°.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated to dryness in vacuo
  3. filtrationfiltered
  4. customdried
  5. customrecrystallized from C6H6

Sources & evidence

ORD record
ord-09029d4bbc3643578fb9ba0222b64a59
Source dataset
uspto-grants-1976_02
Patent number
US03940404

Reaction notes

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