Methanol → 3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-one

HRID 2101224

Reaction equation

HRID 2101224 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].CO.[CH:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>C(OC(=O)C)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH:14]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 941973-(4-Methoxyphenyl)-1-phenylprop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetophenone (0.5 g) and sodium hydroxide (0.17 g) were suspended in 15 Ml of methanol pre-chilled at −10° C. p-Anisaldehyde (0.57 g) was added thereto, and stirred for 10 hr at room temperature. After neutralization with 5% hydrochloric acid solution, the product was extracted with 100 Ml of ethylacetate. The extracted organic phase was dried with anhydrous magnesium sulfate, and concentrated under vacuum evaporator. Purified compound was obtained by elution with n-hexane:ethylacetate (v/v, 1:7) through silica gel column chromatography (5×3 cm, Merk), and identified as follows:

Workup

  1. additionwas added
  2. extractionAfter neutralization with 5% hydrochloric acid solution, the product was extracted with 100 Ml of ethylacetate
  3. dry with materialThe extracted organic phase was dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum evaporator
  5. customPurified compound was obtained by elution with n-hexane

Sources & evidence

ORD record
ord-6be23af2371049c49a375372ad07cdd3
Source dataset
uspto-grants-2009_08
Patent number
US07572831B2

Linked notes

Loading…