Hydrochloric Acid → (E)-N-(4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenyl)acetamide

HRID 884663Notes

Reaction equation

HRID 884663 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[CH3:14])(=[O:3])[CH3:2].[OH-].[Na+].[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[CH3:26].Cl>CCO.O>[OH:17][C:18]1[CH:25]=[CH:24][C:21](/[CH:22]=[CH:2]/[C:1]([C:4]2[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=2[CH3:14])=[O:3])=[CH:20][C:19]=1[CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 2737381N-(4-Acetyl-3-methylphenyl)acetamide

Product 1

HCID 59349186(E)-N-(4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of N-(4-acetyl-3-methylphenyl)acetamide (1.3 g, 7.0 mmol) and NaOH (1.4 g, 36 mmol) in 25 mL of absolute EtOH was added 4-hydroxy-3-methylbenzaldehyde (1.0 g, 7.3 mmol). The reaction mixture was stirred at room temperature for 18 hr. 5 mL of water was added and the reaction mixture was acidified with concentrated HCl to pH 5-6. The aqueous layer was extracted with two 25 mL portions of EOAc, and the layers were separated. The organic layer was dried with Na2SO4, filtered and concentrated under reduced pressure. The resulting product was submitted to the next step without further purification.

Workup

  1. extractionThe aqueous layer was extracted with two 25 mL portions of EOAc
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting product was submitted to the next step without further purification

Sources & evidence

ORD record
ord-bf73e818b71a49028d1c0b7101c0d143
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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