Benzaldehyde → Ccris 2231

HRID 1287417

Reaction equation

HRID 1287417 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].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>C(O)C>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 74764'-Methoxyacetophenone2×HCID 14798Sodium Hydroxide

Product 1

HCID 92853Ccris 2231Yield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50.1 g. (0.333 m) 4-methoxyacetophenone and 35.4 g (0.333 m) benzaldehyde were combined in a 500 ml Erlenmeyer flask, with the 4-methoxyacetophenone being previously melted. Then 80 ml 5N NaOH solution (appr.) (1.2 × 0.333 m) was added to the mixture. Approximately 40 ml absolute ethanol was added to the stirred mixture in small portions to keep the mixture homogeneous. It was let stir at room temperature overnight, and a solid white cake resulted. The solid was filtered, washed with water, and then recrystallized from methanol/water to give 72.3 g (91%) of 1-(4-methoxyphenyl)-3-phenyl-2-propen-1-one. 10 g (0.0420 m) of this compound and 160 mg Pd on C (10%) were combined with about 200 ml ethyl acetate and placed under 1 atm of hydrogen. Upon stirring, the mixture absorbed 950 ml H2 (calc. 940 ml) and stopped. The reaction mixture was filtered and the clear solution was concentrated to obtain 9.8 g (98%) of 1-(4-methoxyphenyl)-3-phenyl-1-propanone.

Workup

  1. customa solid white cake resulted
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-7b6aeeb477794a78b89206bf7879b985
Source dataset
uspto-grants-1976_10
Patent number
US03984501

Linked notes

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