Acetone → Dimethyl 4,4'-(3-oxopenta-1,4-diene-1,5-diyl)dibenzoate

HRID 77665Notes

Reaction equation

HRID 77665 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[CH3:13][C:14]([CH3:16])=[O:15].[OH-:17].[Na+]>CO.O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:13][C:14](=[O:15])[CH:16]=[CH:9][C:8]2[CH:11]=[CH:12][C:5]([C:1]([O:3][CH3:4])=[O:17])=[CH:6][CH:7]=2)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 54403998Dimethyl 4,4'-(3-oxopenta-1,4-diene-1,5-diyl)dibenzoateYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-Carbmethoxybenzaldehyde (1ae, 0.62 g, 3.8 mmol) and acetone (19, 0.14 ml, 1.9 mmol) were combined in methanol (20 ml) and stirred under a nitrogen atmosphere for 15 min at room temperature. A solution of sodium hydroxide (0.15 g, 3.8 mmol) in water (5 ml) was added the mixture stirred for 18 hr at room temperature under a nitrogen atmosphere. The resulting precipitate was filtered and recrystallized from xylene to give 0.29 g (44%) of a yellow solid: mp 206-210° C. [expected mp 221-223° C.]; 1H NMR: δ 3.92 (s, 6H), 7.12 (d, 2H, J=16.1 Hz), 7.65 (d, 4H, J=8.1 Hz), 7.73 (d, 2H, J=15.9 Hz), 8.06 (d, 4H, J=8.0 Hz); 13C NMR: δ 52.3, 127.1, 128.1, 130.1, 131.6, 138.8, 142.1, 166.2, 188.0.

Workup

  1. stirringstirred for 18 hr at room temperature under a nitrogen atmosphere
  2. filtrationThe resulting precipitate was filtered
  3. customrecrystallized from xylene

Sources & evidence

ORD record
ord-c76f7e2187c14905bacf596e8ec673b0
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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