4-Fluorobenzaldehyde → HCID 178445612, compound

HRID 2254942Notes

Reaction equation

HRID 2254942 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1>[F:18][C:19]1[CH:26]=[CH:25][C:22]([C@H:23]2[O:15][CH2:14][C@H:13]([CH2:12][CH2:11][C@H:8]3[CH2:7][CH2:6][C@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:10][CH2:9]3)[CH2:16][O:17]2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 178445610HCID 178445610, compound

Product 1

HCID 178445612HCID 178445612, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.4 g (0.01 mol) of 2-[2'-(trans-4"- butylcyclohexyl)ethyl]propane-1,3-diol, 1.8 g (0.01 mol) of 4-fluorobenzaldehyde (manufactured by Aldrich) and 0.1 g of TsOH in 50 cm3 of dichloromethane was refluxed for 3 hours over a hot water bath with a Dean-Stark trap. The resulting solution was washed with water and the dichloromethane was distilled off. The residue was recrystallized from a solvent mixture of acetone and methanol to yield 3.0 g (0.008 mol) of trans-2-(4'-fluorophenyl)-5-[2'-(trans-4"-butylcyclohexyl)ethyl]-1,3-dioxane. The phase transition temperature of this compound, measured by DSC, was: ##STR41## wherein C is the crystal phase, N is the nematic phase, and I is the isotropic liquid phase.

Workup

  1. washThe resulting solution was washed with water
  2. distillationthe dichloromethane was distilled off
  3. customThe residue was recrystallized from a solvent mixture of acetone and methanol

Sources & evidence

ORD record
ord-04888a890d3e421ab05b0ab5dce39c44
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

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