Benzaldehyde → 1,4-Pentadien-3-one, 1-(4-methoxyphenyl)-5-phenyl-, (E,E)-

HRID 77677

Reaction equation

HRID 77677 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[OH-].[Na+].O.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:13])[CH:12]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 954144-(4-Methoxyphenyl)but-3-en-2-one

Product 1

HCID 7605101,4-Pentadien-3-one, 1-(4-methoxyphenyl)-5-phenyl-, (E,E)-Yield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-Methoxyphenyl)-1-buten-3-one (35e, 0.29 g, 1.6 mmol) was dissolved in methanol (5 ml) and stirred for 5 min at room temperature. A solution of sodium hydroxide (0.14 g, 3.5 mmol) and water (5 ml) was added and the mixture stirred for 30 min at room temperature. Benzaldehyde (1b, 0.17 ml, 1.7 mmol) was added dropwise and the mixture stirred for 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethanol to give 0.41 g (94%) of a yellow solid: mp 85-89° C. [expected mp 118-119° C.]; 1H NMR: δ 3.82 (s, 3H), 6.91 (d, 2H, J=8.5 Hz), 6.94 (d, 1H, J=15.9 Hz), 7.06 (d, 1H, J=16.1 Hz), 7.38 (m, 4H), 7.57 (m, 3H), 7.71 (dd, 2H, J=15.9, 2.0 Hz); 13C NMR: δ 55.4, 114.4, 123.3, 125.5, 127.4, 128.2, 128.8, 130.0, 130.2, 134.8, 142.6, 143.0, 161.5, 188.6.

Workup

  1. stirringthe mixture stirred for 30 min at room temperature
  2. stirringthe mixture stirred for 18 hr at room temperature
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5f6605a5b4044f2f810367de70af7ec3
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Linked notes

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