Sodium Hydroxide → HCID 54231235, compound

HRID 1534683Notes

Reaction equation

HRID 1534683 reaction equation
[CH2:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH:20]=[CH:19][C:18]=1[C:29](=[O:31])[CH3:30].[OH-].[Na+]>C(O)(C)C.O>[CH2:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[CH:30][C:29]([C:18]1[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:22][C:17]=1[OH:16])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 109329682'-Hydroxy-4'-(3-methyl-2-butenyloxy)acetophenoneHCID 18417656HCID 18417656, compound

Product 1

HCID 54231235HCID 54231235, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 3.11 g of 2-heptylbenzaldehyde and 3.35 g of 2'-hydroxy-4'-(3-methyl-2-butenyloxy)-acetophenone in 65 ml of isopropanol was added a solution of 2.9 g of sodium hydroxide in 6 ml of water under a nitrogen atmosphere, and the mixture was stirred at 45° C. for 8 hours. After neutralization with dilute hydrochloric acid with ice cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography with n-hexane including 1% ethyl acetate. The resulting fractions containing the end compound was recrystallized from isopropanol to give 3.23 g of 2-n-heptyl-2'-hydroxy-4'-(3-methyl-2-butenyloxy)-chalcone as yellow needles.

Workup

  1. extractionAfter neutralization with dilute hydrochloric acid with ice cooling, the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography with n-hexane including 1% ethyl acetate
  6. additionThe resulting fractions containing the end compound
  7. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-14c7f836cf2a448d944851c28c111bac
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

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