HCID 59316794, Verbindung → 3-Bromo-4-propan-2-yloxybenzoic acid

HRID 423310

Reaktionsgleichung

Reaktionsgleichung von HRID 423310
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])[C:5]([O:7]C(C)C)=[O:6]>C(O)C.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])[C:5]([OH:7])=[O:6]

Komponenten

4

Edukt 1

HCID 59316794HCID 59316794, Verbindung

Produkt 1

HCID 166412393-Bromo-4-propan-2-yloxybenzoic acidAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 1-methylethyl 3-bromo-4-[(1-methylethyl)oxy]benzoate (D20) (2.36 g, 7.84 mmol) in ethanol (100 mL) and aqueous sodium hydroxide (2M, 39 mL) was heated to reflux for 5 h. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate (125 mL) and water (125 mL), the latter acidified with 2M HCl (40 mL). The aqueous layer was extracted with further ethyl acetate (70 mL) and the combined organic extracts dried (phase separator) and concentrated in vacuo to give the title compound as an off-white solid (1.83 g, 7.06 mmol). δH (methanol-d4, 400 MHz): 8.05 (1H, d), 7.89 (1H, dd), 7.23 (1H, d), 4.79 (1H, septet), 1.32 (6H, d). MS (ES): C10H11BrO3 requires 258, 260; found 257, 259 (M−H+).

Aufarbeitung

  1. temperatureto reflux for 5 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate (125 mL) and water (125 mL)
  4. extractionThe aqueous layer was extracted with further ethyl acetate (70 mL)
  5. customthe combined organic extracts dried (phase separator)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5c607905d4ab44b29efe6001a7200569
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101775B2

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