3-Hydroxy-4-methoxybenzeneacetic acid → Ethyl 2-(3-hydroxy-4-methoxyphenyl)acetate

HRID 516819

Reaktionsgleichung

Reaktionsgleichung von HRID 516819
[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].O.[C:15]1(C)C=CC(S(O)(=O)=O)=C[CH:16]=1>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH2:15][CH3:16])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Komponenten

4

Edukt 2

HCID 1605623-Hydroxy-4-methoxybenzeneacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 5324706Ethyl 2-(3-hydroxy-4-methoxyphenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The stirred solution of 2-(3-Hydroxy-4-methoxyphenyl)acetic acid (9.82 g, 53.90 mmol) and p-Toluenesulfonic acid monohydrate (1.15 g, 6.0 mmol) in abs ethanol (100 ml) was refluxed for 4 hours or until all the starting material is consumed. The reaction mixture was concentrated, diluted with ethyl acetate and washed with 1M HCl. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound.

Aufarbeitung

  1. customis consumed
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with 1M HCl
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ed32896d4477471a8d470190ed294692
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115072B2

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