p-Toluenesulfonic acid monohydrate → ((1-(Benzyloxy)-3-chloropropan-2-yl)oxy)methyl propionate

HRID 324712

Reaktionsgleichung

Reaktionsgleichung von HRID 324712
[CH2:1]([O:8][CH2:9][CH:10]([OH:13])[CH2:11][Cl:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:18][CH2:19]OC)(=[O:17])[CH2:15][CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCCCCC>[CH2:1]([O:8][CH2:9][CH:10]([O:13][CH2:19][O:18][C:14](=[O:17])[CH2:15][CH3:16])[CH2:11][Cl:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 41410061-Benzyloxy-3-chloro-2-propanolHCID 11228781Methoxymethyl propionate

Produkt 1

HCID 11358151((1-(Benzyloxy)-3-chloropropan-2-yl)oxy)methyl propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

204.0 g of 3-benzyloxy-1-chloro-2-propanol, 660 ml of hexane, 626.3 g of methoxymethyl propionate and 5.79 g of p-toluenesulfonic acid mono-hydrate were placed into a 2-liter 3-neck round bottom flask equipped with a thermometer, mechanical stirrer, nitrogen inlet and an efficient distillation column. The reaction mixture was heated to reflux. The distillate was taken off at about 10:1 to 15:1 reflux ratio keeping the head temperature below 60° C. Samples were taken to monitor the progress of the reaction. The reaction was quenched when the desired level of methyl acetal was reached which is usually less than about 4% methyl acetal. The quench was carried out by rapidly adding a solution of 11.55 g of sodium carbonate in 310 ml of water directly to the hot reaction mixture. The aqueous layer was washed with additional water and/or base to remove any residual propionic acid. The volatiles were removed to leave the crude product as a mobile liquid. Yield: 285.2 g, (97.8%); 92.6% pure.

Aufarbeitung

  1. customequipped with a thermometer, mechanical stirrer, nitrogen inlet
  2. distillationan efficient distillation column
  3. temperatureThe reaction mixture was heated to reflux
  4. temperaturereflux ratio
  5. customthe head temperature below 60° C
  6. customthe progress of the reaction
  7. customThe reaction was quenched when the desired level of methyl acetal
  8. additionby rapidly adding a solution of 11.55 g of sodium carbonate in 310 ml of water directly to the hot reaction mixture
  9. washThe aqueous layer was washed with additional water and/or base
  10. customto remove any residual propionic acid
  11. customThe volatiles were removed

Quellen und Nachweise

ORD-Eintrag
ord-60e05651615c4e74acce2f9c86afca20
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218568B1

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