Acetone → 1,5-Bis-(4-benzyloxy-phenyl)-penta-1,4-dien-3-one

HRID 356450Notes

Reaction equation

HRID 356450 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([CH3:20])=[O:19].[OH-:21].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:16][C:9](=[O:21])[CH:10]=[CH:11][C:12]2[CH:15]=[CH:20][C:18]([O:19][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:17][CH:13]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Product 1

HCID 4714751,5-Bis-(4-benzyloxy-phenyl)-penta-1,4-dien-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared as described in General Method 1 using 42.4 g (0.2 mol) 4-benzyloxybenzaldehyde, 700 mL absolute ethanol (EtOH), 5.8 g (0.1 mol) acetone and 10 mL 10% NaOH. The reaction was refluxed for 2 hours. After cooling the reaction was filtered, and the resultant solid dried. It was used without further purification in the next reaction. 1H NMR (CDCl3) δ 5.11 (s, 4 H), 6.91-7.01 (m, 6 H), 7.34-7.45 (m, 10 H), 7.57 (m, 4 H), 7.69 (d, 2 H).

Workup

  1. temperatureThe reaction was refluxed for 2 hours
  2. temperatureAfter cooling the reaction
  3. filtrationwas filtered
  4. customthe resultant solid dried
  5. customIt was used without further purification in the next reaction

Sources & evidence

ORD record
ord-f2f145e690574a919bfda8cca5a19c36
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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