Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate → HCID 59509487, Verbindung

HRID 2407473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407473
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][C:13]([CH3:15])=[CH2:14])[CH:6]=1)[CH3:2]>C(O)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]2[O:11][C:13]([CH3:15])([CH3:14])[CH2:12][C:7]=2[CH:6]=1)=[O:16])[CH3:2]

Komponenten

3

Edukt 1

HCID 18705333Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

Produkt 1

HCID 59509487HCID 59509487, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of formic acid (12 mL) and 4-hydroxy-3-(2-methylprop-2-enyl)benzoic acid ethyl ester (4.8 g, 0.022 mol) is heated at 110° C. for 15 minutes. The reaction mixture is cooled to room temperature and formic acid is removed under reduced pressure. Demineralized water is added to the residue and the aqueous layer is extracted with dichloromethane (3×15 mL). Combined organic layers are washed with demineralized water (1×15 mL) followed by brine (1×15 mL) and dried over sodium sulphate. Removal of solvent gives a viscous liquid which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 90:10) to give 2,2-dimethyl-2,3-dihydro-1-benzofuran-5-carboxylic acid ethyl ester.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customformic acid is removed under reduced pressure
  3. additionDemineralized water is added to the residue
  4. extractionthe aqueous layer is extracted with dichloromethane (3×15 mL)
  5. washCombined organic layers are washed with demineralized water (1×15 mL)
  6. dry with materialdried over sodium sulphate
  7. customRemoval of solvent
  8. customgives a viscous liquid which
  9. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-d44d9b3fb5a6405b95a1653d12cc8f13
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809539B2

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