4'-Methoxyacetophenone → HCID 4363702, compound

HRID 651298Notes

Reaction equation

HRID 651298 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[CH3:12][C:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([CH3:15])[CH3:14].[OH-].[Na+]>CO>[CH3:15][C:13]([C:16]1[CH:17]=[CH:18][C:19]([CH:20]=[CH:1][C:2]([C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=2)=[O:3])=[CH:22][CH:23]=1)([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 74764'-MethoxyacetophenoneHCID 14798Sodium HydroxideHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 4363702HCID 4363702, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

97.6 g (0.65 mol) of 4-methoxyacetophenone and 105.4 g (0.65 mol) of 4-(1,1-dimethylethyl)benzaldehyde were dissolved in 600 ml of methanol in a 1 1 round-bottom flask fitted with internal thermometer, reflux condenser and paddle stirrer. 20 g (0.05 mol) of 10% NaOH were then added at room temperature. The mixture was then stirred at 30° C. The crystals which formed were filtered off, washed with 50 ml of cold methanol and then dried under reduced pressure (150 mbar) at 75° C. Yield: 172 g (90% yield) of pale yellow crystals; m.p.: 114-116° C.; purity: >99%.

Workup

  1. customfitted with internal thermometer
  2. temperaturereflux condenser and paddle stirrer
  3. customThe crystals which formed
  4. filtrationwere filtered off
  5. washwashed with 50 ml of cold methanol
  6. customdried under reduced pressure (150 mbar) at 75° C

Sources & evidence

ORD record
ord-82696f2f4b384248b2482506a718cddf
Source dataset
uspto-grants-2001_08
Patent number
US06278025B1

Reaction notes

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