Trifluoroacetic acid → HCID 12792607, compound

HRID 1154773Notes

Reaction equation

HRID 1154773 reaction equation
[CH3:1][C:2]([CH:4]1[CH2:21][CH2:20][C:19]2[CH:18]3[O:22][CH:7]([C:8]4[C:17]3=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=4)[C:6]=2[CH2:5]1)=[O:3].FC(F)(F)C(O)=[O:26].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:2]([CH:4]1[CH2:21][CH2:20][C:19]2[C:18](=[O:26])[C:17]3[C:8](=[CH:9][C:10]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:7](=[O:22])[C:6]=2[CH2:5]1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 13377216HCID 13377216, compound

Product 1

HCID 12792607HCID 12792607, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.68 g of (1,2,3,4,5,12-hexahydro-5,12-epoxynaphthacen-2-yl) methyl ketone, 15 ml of chloroform and 0.9 ml of trifluoroacetic acid was left to stand at room temperature for 20 hours, neutralised with sodium hydrogen carbonate and extracted with methylene chloride. The extract was dried over sodium sulphate and concentrated to dryness. The residue was treated with 50 ml of methylene chloride, 1 ml of diethyl ether and 12 g of silicic acid and the mixture was stirred in the air for 48 hours. After concentration to dryness, the residue was chromatographed on silicic acid. There were obtained 475 g (38%) of crude 2-acetyl-1,2,3,4-tetrahydro-5,12-naphthacenedione which, after washing with methanol, had a melting point of 189°-192° C. (from ethanol).

Workup

  1. waitwas left
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried over sodium sulphate
  4. concentrationconcentrated to dryness
  5. additionThe residue was treated with 50 ml of methylene chloride, 1 ml of diethyl ether and 12 g of silicic acid
  6. concentrationAfter concentration to dryness
  7. customthe residue was chromatographed on silicic acid

Sources & evidence

ORD record
ord-7c46121c99bc4e73ba828ef88001f1cf
Source dataset
uspto-grants-1981_11
Patent number
US04298535

Reaction notes

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