p-Toluenesulfonic acid → HCID 178445608, compound

HRID 2254944Notes

Reaction equation

HRID 2254944 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].[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[F:27].CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]2[O:15][CH2:14][CH: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][C:20]=1[F:27]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 178445610HCID 178445610, compound

Product 1

HCID 178445608HCID 178445608, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.1 g (0.025 mol) of 2-[2'-(trans-4"-butylcyclohexyl)ethyl]propane-1,3-diol, 5.1 g (0.025 mol) of 4-bromo-3-fluorobenzaldehyde, and g of TsOH in 125 cm3 of dichloromethane was refluxed for 5 hours over a hot water bath with a Dean-Stark trap. The 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 8.4 g (0.02 mol) of 2-(4'-bromo-3'-fluorophenyl)-5-[2'-(trans-4"-butylcyclohexyl)ethyl]-1,3-dioxane.

Workup

  1. washThe 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-5a18bf576b22428da9bc035a112fd731
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

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