Tetrahydrofuran → Methyl 4-(2-hydroxyethyl)benzoate

HRID 2120616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120616
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][CH:5]=1.B1C2CCCC1CCC2.[O:22]1CCCC1>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:22])=[CH:6][CH:5]=1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 583124Methyl 4-ethenylbenzoate

Produkt 1

HCID 14078904Methyl 4-(2-hydroxyethyl)benzoateAusbeute 64,7 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl-4-vinylbenzoate 70 (2.270 g, 14.00 mmol) was dissolved in 50 ml of tetrahydrofuran and cooled to 0° C. 9-BBN (0.5M in THF)(28.00 ml, 14.00 mmol) was added and the mixture was stirred for 2 hours. The solution was allowed to warm to room temperature and stirred for an additional 2 hours. The reaction was cooled to 0° C. and quenched with alkaline hydrogen peroxide. The mixture was then extracted with diethyl ether. The extracts were dried over anhydrous sodium sulfate and concentrated en vacuo. The residue was purified by flash chromatography on silica eluted with 4:1 hexane/acetone to give 1.632 g (64.7%) of 4-(2-hydroxyethyl)benzoic acid methyl ester 71 as a clear oil.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional 2 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with alkaline hydrogen peroxide
  5. extractionThe mixture was then extracted with diethyl ether
  6. dry with materialThe extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated en vacuo
  8. customThe residue was purified by flash chromatography on silica
  9. washeluted with 4:1 hexane/acetone

Quellen und Nachweise

ORD-Eintrag
ord-e3efc9765b294632bf620bdc8c409338
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693098B2

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