Sodium Methoxide → Ethyl (4-hydroxy-2-methylphenoxy)acetate

HRID 1909573

Reaktionsgleichung

Reaktionsgleichung von HRID 1909573
C([O:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:18])[CH:6]=1)(=O)C.C[O-].[Na+]>CO>[OH:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:18])[CH:6]=1

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 21986316Ethyl 2-(4-acetoxy-2-methylphenoxy)acetate

Produkt 1

HCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(4-acetoxy-2-methylphenoxy)acetate (684) (6.79 g, 27 mmol) in dry methanol (150 mL) was added sodium methoxide (1.1 eq.) and the reaction was stirred at room temperature under N2 for 3 hours. The reaction was quenched with 1M HCl and the volatiles were removed in vacuo. The oil was dissolved in ethyl acetate (100 mL) and washed with water (2×100 mL), and brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afforded ethyl 2-(4-hydroxy-2-methylphenoxy)acetate (685) as a white solid (77%).

Aufarbeitung

  1. customThe reaction was quenched with 1M HCl
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe oil was dissolved in ethyl acetate (100 mL)
  4. washwashed with water (2×100 mL), and brine (100 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-005beb8f47bd4b219cb7d084b744053a
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598374B2

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