Water → HCID 178448076, compound

HRID 2254931Notes

Reaction equation

HRID 2254931 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]([CH2:13][OH:14])[CH2:11][OH:12])[CH2:6][CH2:5]1)[CH2:2][CH3:3].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>ClCCl>[F:15][C:16]1[CH:23]=[CH:22][C:19]([C@H:20]2[O:12][CH2:11][C@H:10]([C@H:7]3[CH2:8][CH2:9][C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]3)[CH2:13][O:14]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 680234-FluorobenzaldehydeHCID 112294182-(4-Propylcyclohexyl)propane-1,3-diol

Product 1

HCID 178448076HCID 178448076, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 40 cm3 of dichloromethane, 1.5 g (0.008 mol) of 2-(4'-propylcyclohexyl) propane-1,3-diol, 1.4 g (0.01 mol) of 4-fluorobenzaldehyde (manufactured by Aldrich), and 0.1 g of TsOH were refluxed for 3 hours over a hot water bath fitted with a Dean-Stark trap and the water formed was continuously removed from the reaction system. The reaction solution was washed with water and the dichloromethane was distilled off. The distillation residue was recrystallized from a solvent mixture of acetone and methanol to yield 1.1 g (0.004 mol) of trans-2-(4'-fluorophenyl)-5-(trans-4'-propylcyclohexyl)-1,3-dioxane. The phase transition points of this compound, measured by DSC, were: ##STR25## wherein C is the crystal phase, N is the nematic phase and I is the isotropic liquid phase.

Workup

  1. customfitted with a Dean-Stark trap
  2. customwas continuously removed from the reaction system
  3. washThe reaction solution was washed with water
  4. distillationthe dichloromethane was distilled off
  5. customThe distillation residue was recrystallized from a solvent mixture of acetone and methanol

Sources & evidence

ORD record
ord-b461fb89736440c09a947125bd237b11
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

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