Ethanol → HCID 2806014, compound

HRID 1380519Notes

Reaction equation

HRID 1380519 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH3:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21].C(O)C>CCOCC>[CH3:19][N:20]([CH3:22])[CH:21]=[CH:10][C:8](=[O:9])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 699071,1-DiphenylacetoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 2806014HCID 2806014, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 21.0 g of 1,1-diphenylacetone and 40 ml of N,N-dimethylformamide dimethyl acetal in a 300 ml round bottom flask was heated in an oil bath at 120° C. for 8 hours with ethanol being distilled over. The reaction mixture was cooled and evaporated in vacuo to give an oil. The oil was boiled up in 50 ml of ether then cooled at -10° C. and gave a heavy precipitate. The precipitate was collected, washed with ether, then air dried and gave 21.5 g of crude product. A 5.0 g portion was recrystallized from 50 ml of 2-propanol, then cooled at room temperature. The material was collected and dried at 60° C. and gave 1.7 g of the desired product, mp 93°-94° C.

Workup

  1. distillationdistilled over
  2. temperatureThe reaction mixture was cooled
  3. customevaporated in vacuo
  4. customto give an oil
  5. customgave a heavy precipitate
  6. customThe precipitate was collected
  7. washwashed with ether
  8. customair dried
  9. customgave 21.5 g of crude product
  10. customA 5.0 g portion was recrystallized from 50 ml of 2-propanol
  11. temperaturecooled at room temperature
  12. customThe material was collected
  13. customdried at 60° C.

Sources & evidence

ORD record
ord-48bd0760a1c54d87aeb69433f4654cc2
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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