Toluene → 2-(3-Chloropropyl)-2,5,5-trimethyl-1,3-dioxane

HRID 2085477Notes

Reaction equation

HRID 2085477 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[CH3:8][C:9]([CH3:14])([CH2:12]O)[CH2:10][OH:11].C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([CH3:6])[O:11][CH2:10][C:9]([CH3:14])([CH3:12])[CH2:8][O:7]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 31344Neopentyl glycolHCID 799932-Pentanone, 5-chloro-

Product 1

HCID 131998902-(3-Chloropropyl)-2,5,5-trimethyl-1,3-dioxane

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent2×

Procedure

A one liter, round bottom flask is equipped with a magnetic stir bar, a Dean-Stark water separator, a reflux condenser and a nitrogen inlet. This apparatus is dried in an oven overnight at 120° C., assembled hot, and is allowed to cool to room temperature in a stream of nitrogen. The flask is charged with 144.70 grams (1.20 moles) of 5-chloro-2-pentanone, 185.00 grams (1.32 moles) of 2,2-dimethyl-1,3-propandiol, 300 ml of toluene and 0.05 grams of p-toluenesulfonic acid catalyst. The flask is placed in a heating mantle and the reaction mixture is heated to reflux until close to the theoretical amount of water (21.6 ml) is collected in the Dean-Stark trap. The reaction mixture is allowed to cool to room temperature, transferred to a separatory funel and washed with 200 ml portions of saturated sodium bicarbonate solution, and three times with water. The resulting organic layer is separated, dried over anhydrous potassium carbonate, filtered, and concentrated under reduced pressure on a rotary evaporator. This affords a clear, pale yellow oil, which is employed in the subsequent reactions without further purification.

Workup

  1. customA one liter, round bottom flask is equipped with a magnetic stir bar
  2. customThis apparatus is dried in an oven overnight at 120° C.
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux
  5. customis collected in the Dean-Stark trap
  6. temperatureto cool to room temperature
  7. washwashed with 200 ml portions of saturated sodium bicarbonate solution, and three times with water
  8. customThe resulting organic layer is separated
  9. dry with materialdried over anhydrous potassium carbonate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure on a rotary evaporator
  12. customThis affords a clear, pale yellow oil, which
  13. customis employed in the subsequent reactions without further purification

Sources & evidence

ORD record
ord-816a69687fae4902a4bb27341ea17028
Source dataset
uspto-grants-2004_04
Patent number
US06720391B2

Reaction notes

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