Cyclohexanone → 2,6-Bis-(4-hexyloxy-benzylidene)-cyclohexanone

HRID 495321

Reaction equation

HRID 495321 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:8].[Na+].[CH2:10]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>C(O)C.O>[CH2:10]([O:7][C:1]1[CH:6]=[CH:5][C:4]([CH:21]=[C:20]2[CH2:23][CH2:24][CH2:17][C:18](=[CH:21][C:20]3[CH:23]=[CH:24][C:17]([O:16][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:18][CH:19]=3)[C:19]2=[O:8])=[CH:3][CH:2]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 79816p-(Hexyloxy)benzaldehyde

Product 1

HCID 694979802,6-Bis-(4-hexyloxy-benzylidene)-cyclohexanone

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

Cyclohexanone (2.6 ml, 0.025 mol) was dissolved in ethanol (5 ml), and was added to sodium hydroxide (0.38 g, 0.01 mol) dissolved in water (6 ml) and ethanol (2 ml) and was left to stir for 20 min. 4-Hexyloxybenzaldehyde (10 ml, 0.048 mol), dissolved in ethanol (40 ml), was added and the mixture was stirred at room temperature for 16 h. A yellow crystalline solid was isolated by vacuum filtration and was washed with cold ethanol and dried in a vacuum oven. Yield=4.32 g, 36%. 1H NMR and 13C NMR showed expected signals.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 16 h
  3. customA yellow crystalline solid was isolated by vacuum filtration
  4. washwas washed with cold ethanol
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-affe587f4e1d4c599e66c79b12e2f716
Source dataset
uspto-grants-2005_09
Patent number
US06939479B2

Linked notes

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