Sodium Hydroxide → 7-Methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid

HRID 1643843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643843
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7]=2[CH:6]=[C:5]([C:14]([O:16]C)=[O:15])[CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7]=2[CH:6]=[C:5]([C:14]([OH:16])=[O:15])[CH:4]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59560140Methyl 7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylate

Produkt 1

HCID 595602947-Methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acidAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylate (40 g, 0.17 mol) in MeOH (200 mL) was added NaOH (34 g, 0.85 mol) in one portion. The mixture was stirred at room temperature for 24 h. TLC (EtOAc/petroleum ether=1/1) showed the reaction was complete. Then MeOH was removed under vacuum. The residue was dissolved in water (100 mL), and the solution was acidified with conc. HCl. The solid was filtered and the filter cake was dried in vacuo to give the title compound (25 g, 68%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.62 (s, 1H), 7.54 (s, 1H), 3.94 (s, 3H), 3.00 (s, 2H), 1.50 (s, 6H).

Aufarbeitung

  1. customThen MeOH was removed under vacuum
  2. dissolutionThe residue was dissolved in water (100 mL)
  3. filtrationThe solid was filtered
  4. customthe filter cake was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-816098c8797f432fb582e0c416fbe006
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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