Hydrochloric Acid → (E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid

HRID 1362621Notes

Reaction equation

HRID 1362621 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1)[CH:6]=O.C([O:19][C:20](=[O:30])[CH2:21]P(OCC)(OCC)=O)C.O.[OH-].[Li+].[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:21]/[C:20]([OH:30])=[O:19])[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a THF (40 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (4.00 g) obtained in Example 1, diethylphosphonoacetic acid ethyl ester (4.00 mL) and lithium hydroxide monohydrate (932 mg) were added one by one, and the reaction solution was agitated overnight at room temperature. 2N sodium hydroxide solution (30 mL) and ethanol (5 mL) were added to the reaction solution after confirming disappearance of the starting materials, and the reaction solution was agitated at room temperature overnight. The reaction solution was cooled to 0° C., 2N hydrochloric acid (30 mL) was added to the reaction solution, and the precipitation consequently deposited was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 4.61 g of the title compound was obtained.

Workup

  1. stirringthe reaction solution was agitated at room temperature overnight
  2. temperatureThe reaction solution was cooled to 0° C.
  3. customthe precipitation
  4. customconsequently deposited was separated
  5. filtrationby filtering with Kiriyama funnel
  6. customThe obtained precipitation
  7. washwas washed with water and ethyl acetate

Sources & evidence

ORD record
ord-b00c06dcfedf4625b14ac83529e5382d
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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