Hydrochloric Acid → Dimethyl 4,4'-((1E,1'E)-1,4-phenylenebis(ethene-2,1-diyl))dibenzoate

HRID 523138Notes

Reaction equation

HRID 523138 reaction equation
C(OP([CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)(OCC)=O)C.[CH:20]1[C:25]([CH:26]=[O:27])=[CH:24][CH:23]=[C:22]([CH:28]=O)[CH:21]=1.[CH3:30][O-:31].[Na+].Cl>C1COCC1>[C:10]1(/[CH:9]=[CH:9]/[C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=2)[CH:19]=[CH:18][C:13](/[CH:14]=[CH:28]/[C:22]2[CH:21]=[CH:20][C:25]([C:26]([O:31][CH3:30])=[O:27])=[CH:24][CH:23]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12173TerephthalaldehydeHCID 10942334Sodium MethoxideHCID 10946061Methyl 4-(diethoxyphosphorylmethyl)benzoate

Product 1

HCID 22725869Dimethyl 4,4'-((1E,1'E)-1,4-phenylenebis(ethene-2,1-diyl))dibenzoateYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Methyl 4-((diethoxyphosphoryl)methyl)benzoate (2.02 g, 7.05 mmol) and terepthaldehyde (0.462 g, 3.44 mmol) in THF (12 mL) was added to a suspension of NaOMe (1.12 g, 20.6 mmol) in THF (70 mL). The reaction was stirred under nitrogen for four hours and was then neutralized with 1M HCl. The resulting suspension was filtered, the collected solid was washed with THF, EtOH, and H2O, then allowed to dry under vacuum to give a yellow solid (1.15 g, 2.88 mmol, 84%). Characterization data matches literature. J. C. Sancho-García, et al., J. Phys. Chem. B, 109:4872-4880 (2005).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe collected solid was washed with THF, EtOH, and H2O
  3. customto dry under vacuum

Sources & evidence

ORD record
ord-de1fcfb7084d46a5a7fc91c7c835bde8
Source dataset
uspto-grants-2016_05
Patent number
US09334304B2

Reaction notes

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