Acetone → 1,5-Bis(2-naphthyl)-1,4-pentadien-3-one

HRID 77670Notes

Reaction equation

HRID 77670 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[CH3:13][C:14]([CH3:16])=[O:15].[OH-].[Na+].O>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:13][C:14](=[O:15])[CH:16]=[CH:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 62012-NaphthalenecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 5924641,5-Bis(2-naphthyl)-1,4-pentadien-3-oneYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Naphthaldehyde (24, 1.56 g, 10.0 mmol) and acetone (19, 0.37 ml, 5.0 mmol) were combined in ethanol (10 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.60 g, 15.0 mmol) and water (10 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethanol to give 1.16 g (69%) of a yellow solid: mp 244-246° C. [expected mp 243-244° C.]; 1H NMR: δ 7.23 (d, 2H, J=15.9 Hz), 7.52 (m, 4H), 7.83 (m, 8H), 7.93 (d, 2H, J=15.9 Hz), 8.03 (s, 2H); 13C NMR: δ 123.6, 125.7, 126.7, 127.3, 127.8, 128.6, 128.7, 130.5, 132.3, 133.3, 134.3, 143.1, 190.0.

Workup

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-13c48a264fe340509e688e1ee0ced5f9
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

Loading…