1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)-3-methoxymandelic acid phenylmethyl ester

HRID 1460252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460252
[C:1]1([CH2:7][O:8][C:9](=[O:21])[CH:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)[OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:23][CH2:24][CH2:25][Cl:26].C(=O)([O-])[O-].[K+].[K+].C([O-])(=O)C(C1C=CC=CC=1)O>CC(C)=O>[C:1]1([CH2:7][O:8][C:9](=[O:21])[CH:10]([OH:11])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:23][CH2:24][CH2:25][Cl:26])=[C:14]([O:19][CH3:20])[CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 3839223Mandelate ionHCID 150203674-Hydroxy-3-methoxymandelic acid (phenylmethyl) ester

Produkt 1

HCID 150203684-(3-Chloropropoxy)-3-methoxymandelic acid phenylmethyl esterAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2.92 g (0.008 mole) of 4-hydroxy-3-methoxymandelic acid (phenylmethyl) ester, 2 ml (0.02 mole) of 1-bromo-3-chloropropane, and 2.80 g (0.02 mole) of potassium carbonate in 40 ml of acetone was heated at reflux for 16 hours under nitrogen atmosphere during which time the solution changed from colorless to light-yellow. TLC (silica gel, hexanes/acetone 4:1) showed that the mandelate derivative had reacted, but 30-40% of unknown impurities had formed. The inorganic materials were separated by filtration, washed with acetone, and the filtrate was concentrated in vacuo at 60° C. to give 3.65 g of crude product. The material was purified by column chromatography (diameter 25 mm, using 80 g of silica gel) eluted with cyclohexane/ethyl acetate (6:1). The fractions containing the product were collected and the solid recrystallized from ethyl ether/hexanes to give 0.637 g (22%) of material as a white powder.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours under nitrogen atmosphere during which time the solution
  3. customhad reacted
  4. custom30-40% of unknown impurities had formed
  5. customThe inorganic materials were separated by filtration
  6. washwashed with acetone
  7. concentrationthe filtrate was concentrated in vacuo at 60° C.
  8. customto give 3.65 g of crude product
  9. customThe material was purified by column chromatography (diameter 25 mm, using 80 g of silica gel)
  10. washeluted with cyclohexane/ethyl acetate (6:1)
  11. additionThe fractions containing the product
  12. customwere collected
  13. customthe solid recrystallized from ethyl ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4d7b3694ce944ed48f67ec310306c3a9
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05070087

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