Propofol → 2-(Chloromethoxy)-1,3-diisopropylbenzene

HRID 1765972

Reaktionsgleichung

Reaktionsgleichung von HRID 1765972
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].[OH-].[Na+].Br[CH2:17][Cl:18]>C1COCC1>[Cl:18][CH2:17][O:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 4943Propofol2×HCID 6333BromochloromethaneHCID 14798Sodium Hydroxide

Produkt 1

HCID 112531472-(Chloromethoxy)-1,3-diisopropylbenzeneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
64 °C

Versuchsvorschrift

A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser and thermometer. It was charged with 17.8 grams (0.10 moles) of 2,6-diisopropylphenol, 200 mL of THF, 8.0 grams (0.20 mole) of sodium hydroxide pellets, and 387 grams (3.0 moles, 194 mL) of bromochloromethane. The reaction mixture was heated to 64° C. and held for 2-3 hours until no more 2,6-diisopropylphenol was present as measured by GC. After cooling to 25° C., the suspension was filtered and the filter cake was washed with THF. The THF was removed by rotary evaporation and the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.) to give 16.9 grams (0.074 moles, 75% yield) of O-chloromethyl 2,6-diisopropyl phenol.

Aufarbeitung

  1. customA four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser
  2. temperatureAfter cooling to 25° C.
  3. filtrationthe suspension was filtered
  4. washthe filter cake was washed with THF
  5. customThe THF was removed by rotary evaporation
  6. distillationthe resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-b50f8bb6ee114b939406bf2d9362992e
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07229978B2

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