Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

HRID 453496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453496
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].OS(O)(=O)=O.[CH3:18]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:18])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1185343-Chloro-4-hydroxyphenylacetic acid

Produkt 1

HCID 92625Methyl 3-chloro-4-hydroxyphenylacetateAusbeute 96 %

Versuchsvorschrift

2-(3-Chloro-4-hydroxyphenyl)acetic acid (5.0 g, 26.8 mmol) was dissolved in 30 mL of MeOH and H2SO4 (0.744 ml, 13.4 mmol) was added dropwise at ambient temperature. The reaction was refluxed for four hours and then concentrated in vacuo. The residue was diluted with 150 mL of EtOAc and washed sequentially with saturated NaHCO3, water, and brine, dried over H2SO4, and concentrated in vacuo to provide methyl 2-(3-chloro-4-hydroxyphenyl)acetate (5.16 g, 96.0% yield) as a semi-opaque thick oil.

Aufarbeitung

  1. temperatureThe reaction was refluxed for four hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 150 mL of EtOAc
  4. washwashed sequentially with saturated NaHCO3, water, and brine
  5. dry with materialdried over H2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4da649f74393410db10e8a8f4b19877f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492437B2

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