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

HRID 714192

Reaction equation

HRID 714192 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-f40a72be7485452496fcd7c32f0222a8
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Linked notes

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