Benzaldehyde → 2-Propen-1-one,1-(5-methyl-2-thienyl)-3-phenyl-

HRID 2165128

Reaction equation

HRID 2165128 reaction equation
[OH-].[Na+].[C:3]([C:6]1[S:7][C:8]([CH3:11])=[CH:9][CH:10]=1)(=[O:5])[CH3:4].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(O)C>[CH3:11][C:8]1[S:7][C:6]([C:3](=[O:5])[CH:4]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 836552-Acetyl-5-methylthiophene

Product 1

HCID 2386072-Propen-1-one,1-(5-methyl-2-thienyl)-3-phenyl-Yield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred solution of 2.2 grams (0.055 mole) of sodium hydroxide in 20 ml of ethanol was cooled to 0° C. and a mixture of 4.0 grams (0.03 mole) of 2-acetyl-5-methylthiophene and 3.1 grams (0.03 mole) of benzaldehyde in 5 ml of ethanol was added dropwise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred for 16 hours. The reaction mixture was poured into aqueous 1N hydrochloric acid and extracted with methylene chloride. The extract was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 4.6 grams of 1-(5-methyl-2-thienyl)-3-phenyl-2-propen-1-one as a solid.

Workup

  1. additionwas added dropwise
  2. additionUpon completion of addition the reaction mixture
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70d25324e4b141e2a8305046095b2240
Source dataset
uspto-grants-1990_07
Patent number
US04939165

Linked notes

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