2-(4-Propylcyclohexyl)propane-1,3-diol → 2-(4'-Bromo-3',5'-difluorophenyl)-5-(4'-propylcyclohexyl)-1,3-dioxane

HRID 1707529Notes

Reaction equation

HRID 1707529 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[C:23]([F:24])=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[F:25]>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:15][C:16]1[C:23]([F:24])=[CH:22][C:19]([CH:20]2[O:12][CH2:11][CH:10]([CH:7]3[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]3)[CH2:13][O:14]2)=[CH:18][C:17]=1[F:25]

Participants

5

Reactant 2

HCID 112294182-(4-Propylcyclohexyl)propane-1,3-diolHCID 234437854-Bromo-3,5-difluorobenzaldehyde

Product 1

HCID 189615332-(4'-Bromo-3',5'-difluorophenyl)-5-(4'-propylcyclohexyl)-1,3-dioxaneYield 60%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

6.0 g (0.03 mol) of 2-(4'-propylcyclohexyl)propane-1,3-diol, 6.6 g (0.03 mol) of 4-bromo-3,5-difluorobenzaldehyde and 0.3 g of TsOH were dissolved in 60 cm3 of dichloromethane, and it was refluxed for 3 hours on a hot water bath while removing the water produced with a Dean-Stark trap. After washing the reactant on water, the dichloromethane was removed. The residue was recrystallized from a solvent mixture of acetone and methanol to obtain 7.3 g (0.018 mol) of 2-(4'-bromo-3',5'-difluorophenyl)-5-(4'-propylcyclohexyl)-1,3-dioxane(trans-cis form mixture).

Workup

  1. temperatureit was refluxed for 3 hours on a hot water bath
  2. customwhile removing the water
  3. customproduced with a Dean-Stark trap
  4. washAfter washing the reactant on water
  5. customthe dichloromethane was removed
  6. customThe residue was recrystallized from a solvent mixture of acetone and methanol

Sources & evidence

ORD record
ord-9cac8b32ff7f4f8482052c813f7a8880
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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