Toluene → HCID 178448153, compound

HRID 2268711Notes

Reaction equation

HRID 2268711 reaction equation
[CH2:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])[CH2:2][CH3:3].[Cl:9][C:10]1[CH:11]=[C:12]([CH2:17][CH2:18][CH:19]=O)[CH:13]=[C:14]([Cl:16])[CH:15]=1.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Cl:9][C:10]1[CH:11]=[C:12]([CH2:17][CH2:18][C@H:19]2[O:8][CH2:7][C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:5][O:6]2)[CH:13]=[C:14]([Cl:16])[CH:15]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 70211562-propylpropane-1,3-diolHCID 183320543-(3,5-Dichlorophenyl)propanal

Product 1

HCID 178448153HCID 178448153, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A solution comprising 18.3 g (155.1 mmol) of 2-propyl-1,3-propanediol, 30.0 g (147.7 mmol) of 3-(3,5-dichlorophenyl)-propionaldehyde, 1.5 g of p-toluenesulfonic acid, and 300 ml of toluene was heated to reflux while taking out the distilled water for 3 hours. After termination of the reaction, the organic layer was washed with a diluted aqueous sodium bicarbonate solution once and water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: toluene) to obtain 32.3 g of a crude trans-2-(2-(3,5-dichlorophenyl)ethyl)-5-propyl-1,3-dioxane. (Yield: 72.1%)

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customfor 3 hours
  4. customAfter termination of the reaction
  5. washthe organic layer was washed with a diluted aqueous sodium bicarbonate solution once
  6. dry with materialwater thrice, and then dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-42b8e955bf384898ac8a85db0a575b6c
Source dataset
uspto-grants-2001_12
Patent number
US06329027B1

Reaction notes

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