Potassium Hydroxide → 2'-Carboxymethoxy-4-n-heptyl-4'-(3-methyl-2-butenyloxy)chalcone

HRID 1534685Notes

Reaction equation

HRID 1534685 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH:9]=[CH:8][C:7]=1[C:18](=[O:20])[CH3:19])([OH:3])=[O:2].[CH2:21]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[OH-].[K+]>C(O)C>[C:1]([CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([CH3:16])[CH3:17])[CH:9]=[CH:8][C:7]=1[C:18](=[O:20])[CH:19]=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:29][CH:30]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 109216344-HeptylbenzaldehydeHCID 13247580{2-Acetyl-5-[(3-methylbut-2-en-1-yl)oxy]phenoxy}acetic acid

Product 1

HCID 537314392'-Carboxymethoxy-4-n-heptyl-4'-(3-methyl-2-butenyloxy)chalcone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.48 9 of 2'-carboxymethoxy-4'-(3-methyl-2-butenyloxy)acetophenone and 2.80 g of 4-n-heptylbenzaldehyde in 120 ml of ethanol was added 3.5 g of potassium hydroxide, and the mixture was stirred for 5 hours. After neutralization with dilute sulfuric acid, the resulting precipitate was collected by filtration, washed with water, dried and recrystallized from ethanol to give 4.10 g of 2'-carboxymethoxy-4-n-heptyl-4'-(3-methyl-2-butenyloxy)chalcone as pale yellow needles.

Workup

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

Sources & evidence

ORD record
ord-f49a8696a5004439a7fc90a89917e970
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

Loading…