Hydrochloric Acid → Methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoate

HRID 577569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577569
[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([C:9]([O:12][CH2:13][CH2:14][O:15]C2CCCCO2)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl>CO>[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([C:9]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86723693methyl 3-bromo-2-methyl-6-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]benzoate

Produkt 1

HCID 86723795Methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoateAusbeute 110 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 3-bromo-2-methyl-6-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]-benzoate (Cpd HH, 162 mg, 0.434 mmol) in MeOH (4 mL) was treated with 6N HCl (0.2 mL) and stirred at room temperature for 30 minutes. The solvent was concentrated in vacuum to 1 mL and the solution partitioned between DCM (25 mL) and NaHCO3 (sat., aq., 25 mL). The organic layer was concentrated under vacuum to give methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoate (126a, 138 mg, 110% yield) as a colorless oil.

Aufarbeitung

  1. concentrationThe solvent was concentrated in vacuum to 1 mL
  2. customthe solution partitioned between DCM (25 mL) and NaHCO3 (sat., aq., 25 mL)
  3. concentrationThe organic layer was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-82e81d7a35d043ebabf23995d0eabdc3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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