1-Indanone → 2-(4-Hexyloxy-benzylidene)-indan-1-one

HRID 22613

Reaction equation

HRID 22613 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].[CH2:13]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C(O)C.O>[CH2:13]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[C:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 67351-IndanoneHCID 14798Sodium HydroxideHCID 79816p-(Hexyloxy)benzaldehyde

Product 1

HCID 688648672-(4-Hexyloxy-benzylidene)-indan-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

1-Indanone (4.17 g, 0.032 mol) was dissolved in ethanol (20 ml), and was added to sodium hydroxide (0.44 g, 0.011 mol) dissolved in water (8 ml) and ethanol (3 ml) and was left to stir for 20 min. 4-(Hexyloxy)benzaldehyde (6.4 ml, 0.031 mol), dissolved in ethanol (35 ml), was added to the mixture and was stirred for 4 hours. The product was isolated by vacuum filtration and was washed with cold ethanol (2×20 ml) and was dried in a vacuum oven. Yield=8.47 g, 85%. 1H NMR and 13C NMR gave expected signals.

Workup

  1. additionwas added to the mixture
  2. stirringwas stirred for 4 hours
  3. customThe product was isolated by vacuum filtration
  4. washwas washed with cold ethanol (2×20 ml)
  5. customwas dried in a vacuum oven
  6. custom1H NMR and 13C NMR gave expected signals

Sources & evidence

ORD record
ord-0a076eed5552481f957a6c3c15c7d65e
Source dataset
uspto-grants-2005_02
Patent number
US06849203B2

Linked notes

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