Acetone → 4-(3-Methoxy-4-ethoxyphenyl)-3-buten-2-one

HRID 38668

Reaction equation

HRID 38668 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH:8]=O.Cl.[CH3:17][C:18]([CH3:20])=[O:19]>C(O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:17][C:18](=[O:19])[CH3:20])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 671164-Ethoxy-3-methoxybenzaldehyde

Product 1

HCID 692481204-(3-Methoxy-4-ethoxyphenyl)-3-buten-2-oneYield 66.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10% sodium hydroxide aqueous (40 ml) was added under stirring to a solution of 3-methoxy-4-ethoxybenzaldehyde (9.09 g, 50 mmol) in acetone (25 ml), 95% ethanol (25 ml) and water (200 ml). The reaction mixture was stirred for 24 hr at room temperature, after the reaction completed, the reaction mixture was neutralized with 6N hydrochloric acid to adjust pH=7.0. The precipitated solid was collected by filtrating and washed with water and ethanol successively, dried, and then recrystallized from 95% ethanol to give 7.38 g of a pale yellow solid, mp: 95-97° C., yield: 66.5%.

Workup

  1. customThe precipitated solid was collected
  2. filtrationby filtrating
  3. washwashed with water and ethanol successively
  4. customdried
  5. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-494e067128284a1eb05853ce0472705c
Source dataset
uspto-grants-2013_09
Patent number
US08524744B2

Linked notes

Loading…