Hydrochloric Acid → HCID 610239, compound

HRID 2402416Notes

Reaction equation

HRID 2402416 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].[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])[CH3:14].C[O-].[Na+].Cl>CO.CCOC(C)=O>[CH3:4][O:3][C:1](=[O:2])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:14][C:13](=[O:15])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 15294Methyl 4-FormylbenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 610239HCID 610239, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-carbomethoxybenzaldehyde (79 mg, 0.48 mmol) and acetophenone (56 L, 0.48 mmol) in anhydrous methanol (1.6 mL), was added neat sodium methoxide (26 mg, 0.48 mmol). The mixture was stirred at room temperature overnight then heated to reflux for 1 hour, cooled down to room temperature and added HCl 1N and EtOAc. The layers were separated and the organic layer dried over anhydrous MgSO4 and filtered. The solvent was evaporated under vacuum to afford a yellow solid, which was recrystallized from acetonitrile/water to give a pale yellow crystalline solid.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled down to room temperature
  4. customThe layers were separated
  5. dry with materialthe organic layer dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated under vacuum
  8. customto afford a yellow solid, which
  9. customwas recrystallized from acetonitrile/water
  10. customto give a pale yellow crystalline solid

Sources & evidence

ORD record
ord-fffe44ab380e4c0a8564b233ae2cb778
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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