Acetic Anhydride → HCID 11049111, compound

HRID 703255Notes

Reaction equation

HRID 703255 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:18]2[C:17](=[O:25])[C:16]3[C:7](=[CH:8][C:9]4[C:14]([CH:15]=3)=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:6](=[O:26])[C:5]=2[CH:4]=1.[C:29]([O-:32])(=O)[CH3:30].[K+].[C:34](OC(=O)C)(=[O:36])[CH3:35]>[Pd].C(OCC)(=O)C>[F:1][C:2]([F:27])([F:28])[C:3]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:18]2[C:5](=[C:6]([O:26][C:29](=[O:32])[CH3:30])[C:7]3[C:16]([C:17]=2[O:25][C:34](=[O:36])[CH3:35])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=3)[CH:4]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 20089846HCID 20089846, compound

Product 1

HCID 11049111HCID 11049111, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.65 mmol of 2,3-bis-(trifluoromethyl)-naphthacene-5,12-dione, 5 ml of ethyl acetate, 4.96 mmol of potassium acetate and 3 ml of acetic anhydride are hydrogenated for 35 minutes at 20°-25° C., with the addition of 0.1 g of Pd/C (5%). The mixture is filtered and the residue is extracted by washing three times with CH2Cl2. The filtrates are evaporated and the residue is recrystallized from CH2Cl2 /pentane. Yield 76% of 2,3-bis-(trifluoromethyl)-5,12-diacetoxynaphthacene; melting point >250°.

Workup

  1. filtrationThe mixture is filtered
  2. extractionthe residue is extracted
  3. washby washing three times with CH2Cl2
  4. customThe filtrates are evaporated
  5. customthe residue is recrystallized from CH2Cl2 /pentane

Sources & evidence

ORD record
ord-348e7bde828843ae84c1ecf0c5bdf7c4
Source dataset
uspto-grants-1991_01
Patent number
US04981962

Reaction notes

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