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

HRID 77654Notes

Reaction equation

HRID 77654 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-:14].[Na+].Cl>C(O)C.O>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:9][C:8](=[O:14])[CH:7]=[CH:6][C:10]1[CH:4]=[CH:3][CH:2]=[CH:13][C:11]=1[OH:12]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 981761,5-Bis(2-hydroxyphenyl)-1,4-pentadien-3-oneYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Hydroxybenzaldehyde (1q, 1.81 ml, 17.0 mmol) and acetone (19, 0.62 ml, 8.4 mmol) were combined in ethanol (15 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.00 g, 25.0 mmol) and water (4 ml) was added and the solution stirred for 1 week at room temperature. The mixture was neutralized with hydrochloric acid (1 N) and the resulting precipitate filtered and recrystallized from ethyl acetate/hexane to give 1.79 g (80%) of a yellow solid: mp 154-157° C. [expected mp 155° C.]; 1H NMR: (DMSO) δ 6.89 (m, 4H), 7.27 (m, 4H), 7.68 (d, 2H, J=7.4 Hz), 7.93 (d, 2H, J=16.1 Hz), 10.22 (s, 2H); 13C NMR: (DMSO) δ 116.1, 119.3, 121.3, 125.3, 128.5, 131.5, 137.6, 156.9, 188.5.

Workup

  1. stirringthe solution stirred for 1 week at room temperature
  2. filtrationthe resulting precipitate filtered
  3. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-451aa0b305a546138e53b364aeb824e0
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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