4-Hydroxybenzaldehyde → 3-Buten-2-one, 4-(4-hydroxyphenyl)-

HRID 38664

Reaction equation

HRID 38664 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([CH3:13])=[O:12]>[OH-].[Na+]>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:10][C:11](=[O:12])[CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 180Acetone

Product 1

HCID 956483-Buten-2-one, 4-(4-hydroxyphenyl)-Yield 70.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

4-Hydroxybenzaldehyde (10 g, 82 mmol) was dissolved in 28 ml of 10% sodium hydroxide aqueous solution, then acetone (20 ml) and 10% sodium hydroxide aqueous solution (40 ml) was added under stirring, and the reaction mixture was stirred for 6 hr at room temperature. separated solid diluted with water until all separated solid dissolved. The reaction mixture was neutralized with hydrochloric acid to pH=7.0. The precipitated solid was collected by filtration and washed with water and ethanol successively. The crude product was recrystallized from ethanol to give 9.3 g of a pale yellow solid, mp: 104-105° C., yield: 70.4%.

Workup

  1. stirringthe reaction mixture was stirred for 6 hr at room temperature
  2. customseparated solid
  3. additiondiluted with water until all separated solid
  4. dissolutiondissolved
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water and ethanol successively
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-f526c903b5bf482daf69f8cfb513b16b
Source dataset
uspto-grants-2013_09
Patent number
US08524744B2

Linked notes

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