(4-Hydroxyphenoxy)acetic acid → 4-(2-Hydroxyethoxy)phenol

HRID 1095106

Reaktionsgleichung

Reaktionsgleichung von HRID 1095106
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.O1CCCC1.B>O1CCCC1>[OH:9][CH2:8][CH2:7][O:6][C:5]1[CH:11]=[CH:12][C:2]([OH:1])=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 15881(4-Hydroxyphenoxy)acetic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 98340144-(2-Hydroxyethoxy)phenolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxyphenoxyacetic acid (4.9 g, 29 mmol) (Aldrich) in anhydrous tetrahydrofuran (30 mL) at 0° C. was added borane tetrahydrofuran (1 M, 90 mL, 90 mmol) dropwise. The reaction mixture was then stirred at room temperature for 2 h. The mixture was concentrated and residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give title compound as a yellow oil (4.2 g, 94%)

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customresidue was partitioned between ethyl acetate and water
  3. customOrganic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a4c573d633b54cccb6a1d78c5d7a90c8
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134001B2

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