O-Xylene → alpha-[((1-Methylcyclohexyl)methoxy)methyl]-1-pyrrolidineethanol

HRID 477447

Reaktionsgleichung

Reaktionsgleichung von HRID 477447
C[CH:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[OH:3].[CH2:10]([CH:12]1[O:14][CH2:13]1)Cl.Cl[Sn](Cl)(Cl)Cl.[OH-].[Na+].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.[C:27]1(C)C(C)=CC=CC=1>>[CH3:27][C:4]1([CH2:2][O:3][CH2:10][CH:12]([OH:14])[CH2:13][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Komponenten

7

Edukt 6

HCID 7237O-XyleneHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 31268PyrrolidineHCID 1378291-Cyclohexylethanol

Produkt 1

HCID 14097063alpha-[((1-Methylcyclohexyl)methoxy)methyl]-1-pyrrolidineethanolAusbeute 55 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A two liter three necked round bottom flask was equipped with a mechanical stirrer, condenser, thermometer, two neck adapter, drying tube and a nitrogen inlet. 1-Methyl-1-cyclohexylmethanol (71.2 g; 0.555 mole) (the compound of Example 7a) was added to the reaction vessel followed by 100 ml of xylene and 43.4 ml (0.555 mole) of epichlorohydrin. The reaction was heated to 50° C. while stirring under nitrogen. 1.45 g (0.0056 mole) of SnCl4 was added. The reaction exothermed suddenly to 140° C. and slowly cooled to 50° C. The reaction was kept at 50° C. in a water bath for 1.5 hr, then cooled to 5°C. with an ice bath. Cold 20% sodium hydroxide (prepared from 40 g of 50% NaOH) was added followed by 47.4 g (0.666 mole) of pyrrolidine. The ice bath was removed, the reaction was heated to reflux for one hr, cooled to RT, diluted with about one liter of water and extracted twice with ether. The combined ether extracts were washed with water, brine, dried over anhydrous potassium carbonate, filtered through dicalite and concentrated in vacuo to give 143.39 g of crude product a light yellow viscous oil. The crude oil was distilled twice to yield 7.6 g (55%) of the title compound, bp 139°-154° C. (0.025 mm).

Aufarbeitung

  1. customthermometer, two neck adapter, drying tube and a nitrogen inlet
  2. customexothermed suddenly to 140° C.
  3. temperatureslowly cooled to 50° C
  4. temperaturecooled to 5°C. with an ice bath
  5. customThe ice bath was removed
  6. temperaturethe reaction was heated
  7. temperatureto reflux for one hr
  8. temperaturecooled to RT
  9. additiondiluted with about one liter of water
  10. extractionextracted twice with ether
  11. washThe combined ether extracts were washed with water, brine
  12. dry with materialdried over anhydrous potassium carbonate
  13. filtrationfiltered through dicalite
  14. concentrationconcentrated in vacuo
  15. customto give 143.39 g of crude product a light yellow viscous oil
  16. distillationThe crude oil was distilled twice

Quellen und Nachweise

ORD-Eintrag
ord-06f1dc2a91b349168091ac5d1cf69be1
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888335

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