Acenaphthene → HCID 20360648, compound

HRID 1578583Notes

Reaction equation

HRID 1578583 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH2:7]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[CH:16]2)[CH:12]=[CH:11][CH:10]=[C:9]3[CH2:8]1>F>[C:4]([C:12]1[C:13]2[C:18]3[C:9]([CH2:8][CH2:7][C:17]=3[CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 6734AcenaphtheneHCID 12661Diketene

Product 1

HCID 20360648HCID 20360648, compound

Reagents, catalysts & solvents 1

HCID 14917Hydrofluoric AcidSolvent

Procedure

42 g (0.5 mol) of diketene were added dropwise to 77 g of acenaphthene (0.5 mole) in 300 ml of anhydrous hydrofluoric acid at -30°C while stirring. The temperature was maintained for 9 hours. The hydrofluoric acid was distilled off under reduced pressure at a temperature of the still of -30°C, the residue was washed until it was free from acid and distilled under reduced pressure. 10 g of unreacted acenaphthene were recovered (87 % conversion). At a transition temperature of 150° - 155°C under 0.4 torr 85 g (82 % of theory) of slightly yellowish 5-acetoacetyl-acenaphthene melting at 59°C were then obtained.

Workup

  1. temperatureThe temperature was maintained for 9 hours
  2. distillationThe hydrofluoric acid was distilled off under reduced pressure at a temperature of the still of -30°C
  3. washthe residue was washed until it
  4. distillationdistilled under reduced pressure
  5. custom10 g of unreacted acenaphthene were recovered (87 % conversion)

Sources & evidence

ORD record
ord-843eae88d65a4e668b3cbbf4581fe91b
Source dataset
uspto-grants-1976_02
Patent number
US03937737

Reaction notes

Loading…