Water → HCID 178445641, compound

HRID 2254946Notes

Reaction equation

HRID 2254946 reaction equation
[CH2:1]([CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]([CH2:14][OH:15])[CH2:12][OH:13])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)#[N:17].CC1C=CC(S(O)(=O)=O)=CC=1.O>ClCCl>[C:16]([C:18]1[CH:25]=[CH:24][C:21]([C@H:22]2[O:13][CH2:12][C@H: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)[CH2:14][O:15]2)=[CH:20][CH:19]=1)#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 660424-CyanobenzaldehydeHCID 404183872-(4-Butylcyclohexyl)propane-1,3-diol

Product 1

HCID 178445641HCID 178445641, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane, 4.6 g (0.02 mol) of 2-(4'-butylcyclohexyl) propane-1,3-diol, 3.2 g (0.024 mol) of 4-cyanobenzaldehyde, and 0.1 g of TsOH were refluxed for three 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'-cyanophenyl)-5-(trans-4'-butylcyclohexyl)-1,3-dioxane. The phase transition points of this compound, measured by DSC, were: ##STR53##

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-828954675cc8479facbe92a51c37c6e0
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

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