2,5-Dihydroxybenzoic acid → 8-(2-Furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate

HRID 424312

Reaktionsgleichung

Reaktionsgleichung von HRID 424312
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)=[O:21].C(#N)C>O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)=[O:21])=[O:5]

Komponenten

5

Edukt 3

HCID 34692,5-Dihydroxybenzoic acidHCID 6342AcetonitrileHCID 590050482-Furylmethyl 8-bromooctanoate

Produkt 1

HCID 590050178-(2-Furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2,5-dihydroxybenzoic acid (4.8 g), 1,8-diazobicyclo[5.5.0]undec-7-ene (4.7 g), 2-furylmethyl 8-bromooctanoate (7.8 g) and acetonitrile (150 ml) was heated, under reflux for 18 h. The cooled reaction mixture was added to water (500 ml) and extracted with ethyl acetate (3×200 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×20 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuum. The residue (8.4 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (5:1) as eluent, to give 8-(2-furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate as colourless oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×200 ml)
  5. washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×20 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuum
  9. customThe residue (8.4 g) was purified by column flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a0d12cd9d8634c1b8714299d4f590676
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08105662B2

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