Acetone → HCID 19881507, compound

HRID 847418Notes

Reaction equation

HRID 847418 reaction equation
[C:1]([C:9]([OH:11])=[O:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]([CH3:15])=[O:14].S(=O)(=O)(O)O>C(O)(=O)C>[C:2]1([C:1]2[C:9](=[O:10])[O:11][C:13]3([CH:15]=[C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:9](=[O:10])[O:14]3)[CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 11915Phenylglyoxylic Acid

Product 1

HCID 19881507HCID 19881507, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Benzoylformic acid, 25 g, and 11.25 g of acetone in 30 g of acetic acid and 45 g of concentrated sulfuric acid were heated at 105° C.-110° C. for 1 hour. After the resulting mixture was cooled to ambient temperature, it was poured onto ice and the mixture was allowed to warm to room temperature. The suspended particles were recovered by filtration and recrystallized from ethanol to give 3,8-diphenyl-2,7-dioxo-1,6-dioxaspiro[4.4]nona-3,8-diene, m.pt. 235°-237° C., as white powder. Infrared and nuclear magnetic resonance spectra of the powder were consistent with this structure.

Workup

  1. additionit was poured onto ice
  2. temperatureto warm to room temperature
  3. filtrationThe suspended particles were recovered by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7aa2b6a11b4f4f4b9b1b6ce83d419ddb
Source dataset
uspto-grants-1992_08
Patent number
US05142022

Reaction notes

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