Water → HCID 178447929, compound

HRID 2254935Notes

Reaction equation

HRID 2254935 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].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[F:24].O>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]2[O:12][CH2:11][CH: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][C:17]=1[F:24]

Participants

6

Reactant 3

HCID 962WaterHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 112294182-(4-Propylcyclohexyl)propane-1,3-diol

Product 1

HCID 178447929HCID 178447929, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.0 g (0.02 mol) of 2-(4'-propylcyclohexyl)propane-1,3-diol, 5.1 g (0.025 mol) of 4-bromo-3-fluorobenzaldehyde, and 0.2 g of TsOH in 100 cm3 of dichloromethane was refluxed over a hot water bath fitted with a Dean-Stark trap for 3 hours and the water formed was continuously removed from the reaction system. The resulting solution was washed with water and dichloromethane was distilled off. The residue was recrystallized from acetone to yield 6.2 g (0.016 mol) of 2-(4'-bromo-3'-fluorophenyl)-5-(trans-4'-propylcyclohexyl)-1,3-dioxane. This compound contained about 10% of the cis isomer of the 1,3-dioxane ring.

Workup

  1. customfitted with a Dean-Stark trap for 3 hours
  2. customwas continuously removed from the reaction system
  3. washThe resulting solution was washed with water and dichloromethane
  4. distillationwas distilled off
  5. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-189fffb88240459b93510808e45c9326
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

Loading…