Water → HCID 178448077, compound

HRID 2254932Notes

Reaction equation

HRID 2254932 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:17]=[C:18]([CH:21]=[CH:22][C:23]=1[F:24])[CH:19]=O.CC1C=CC(S(O)(=O)=O)=CC=1.O>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([C@H:19]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:21]=[CH:22][C:23]=1[F:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 5880883,4-DifluorobenzaldehydeHCID 112294182-(4-Propylcyclohexyl)propane-1,3-diol

Product 1

HCID 178448077HCID 178448077, compoundYield 62.5%

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, 1.5 g (0.01 mol) of 3,4-difluorobenzaldehyde (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 removed continuously 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 1.6 g (0.005 mol) of trans-2-(3',4'-difluorophenyl)-5-(trans-4'-propylcyclohexyl)-1,3-dioxane. The phase transition points, measured by DSC, were: ##STR31## 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 removed continuously 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-dfd4427bed2a4e64ad9bc63e058c39cc
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

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