Potassium Hydroxide → HCID 54478415, compound

HRID 1534686Notes

Reaction equation

HRID 1534686 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH:5]=[CH:4][C:3]=1[C:14](=[O:16])[CH3:15].[C:17]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].[OH-].[K+]>C(O)C>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([CH:25]=[CH:15][C:14]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH:10]=[C:11]([CH3:12])[CH3:13])=[CH:7][C:2]=2[OH:1])=[O:16])=[CH:27][CH:28]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 703244-tert-ButylbenzaldehydeHCID 109329682'-Hydroxy-4'-(3-methyl-2-butenyloxy)acetophenone

Product 1

HCID 54478415HCID 54478415, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 54.4 g of 2'-hydroxy-4'-(3-methyl-2-butenyloxy)acetophenone and 40.0 g of 4-t-butylbenzaldehyde in 1000 ml of ethanol was added 81.2 g of potassium hydroxide, and the mixture was stirred at 40° C. for 19 hours. After neutralization with dilute hydrochloric acid, the resulting precipitate was collected by filtration, washed with water, dried and recrystallized from isopropanol to give 47.6 g of 4-t-butyl-2'-hydroxy-4'-(3-methyl-2-butenyloxy)chalcone as a yellow powder.

Workup

  1. filtrationAfter neutralization with dilute hydrochloric acid, the resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-b03e67acc1e84ed887aeeccf08ce558d
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

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