Acetone → 4-(3-Ethoxy-4-hydroxyphenyl)but-3-en-2-one

HRID 38667

Reaction equation

HRID 38667 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[CH:9]=O)[CH3:4].Cl.[CH3:16][C:17]([CH3:19])=[O:18]>C(O)C.O>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:16][C:17](=[O:18])[CH3:19])[CH:11]=[CH:12][C:13]=1[OH:14])[CH3:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8467EthylvanillinHCID 14798Sodium Hydroxide

Product 1

HCID 692474294-(3-Ethoxy-4-hydroxyphenyl)but-3-en-2-oneYield 70.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10% sodium hydroxide aqueous solution (80 ml) was added under stirring to a solution of 3-ethoxy-4-hydroxybenzaldehyde (16.6 g, 100 mmol) in acetone (50 ml), 95% ethanol (50 ml) and water (400 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 yellow solid was collected by filtration, washed with water and ethanol successively, dried, and then recrystallized from 95% ethanol to give 14.5 g of a yellow crystal, mp: 98-100° C., yield 70.4%.

Workup

  1. filtrationthe precipitated yellow solid was collected by filtration
  2. washwashed with water and ethanol successively
  3. customdried
  4. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-ff7f346f666d4b05a119f33b618adecf
Source dataset
uspto-grants-2013_09
Patent number
US08524744B2

Linked notes

Loading…