m-Phenylenediacetic acid → 2-[3-(2-Hydroxyethyl)phenyl]ethanol

HRID 225788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 225788
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12](O)=[O:13])[CH:8]=[CH:9][CH:10]=1)(O)=[O:2].CSC.B>C1COCC1>[OH:2][CH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 29788m-Phenylenediacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 100807412-[3-(2-Hydroxyethyl)phenyl]ethanolAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (3-carboxymethylphenyl)acetic acid (1.0 g, 5.15 mmol) in THF (100 mL) was added slowly borane dimethyl sulfide (2.3 mL, 30.9 mmol). The resulting solution was stirred overnight (˜18 hours) and then quenched by slowly adding 1N HCl (100 mL). The mixture was then extracted using EtOAc (3×100 mL) and the combined organic layers were washed with saturated NaCl (100 mL), dried over magnesium sulfate, filtered and concentrated under vacuum to provide 750 mg of the title intermediate (87% yield), which was used without further purification.

Aufarbeitung

  1. customquenched
  2. additionby slowly adding 1N HCl (100 mL)
  3. extractionThe mixture was then extracted
  4. washthe combined organic layers were washed with saturated NaCl (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ee9f825a8395434c80415e717ff5c063
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557126B2

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