Sodium Hydroxide → 2,5-Dimethoxyphenol

HRID 1159426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159426
C([O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[O:13][CH3:14])(=O)C.[OH-].[Na+].OS([O-])(=O)=O.[Na+]>CO>[CH3:14][O:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[OH:4]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 5874512,5-Dimethoxyphenyl acetate

Produkt 1

HCID 53144982,5-DimethoxyphenolAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate 56, 2,5-Dimethoxyphenyl Acetate (13.9 g, 0.07 mol) and NaOH (4.26 g, 0.11 mol) in MeOH (150 mL) was stirred for 12 h in a flow of argon. A 5 M solution of NaHSO4 (21 mL) was added, and the mixture was evaporated. The residue was distributed between CH2Cl2 and H2O (300 mL, 1:1). The aqueous layer was separated, and the product was extracted with CH2Cl2 (2×100 mL). The combined extracts were dried and evaporated to give the title compound (10.8 g, 99%). LCMS data: 156.0 and 155.1 (M+H)+ (calculated for C8H10O3 154.1). 1H NMR data (DMSO-d6): 8.96 (s, 1H, Ar—OH), 6.80 (d, 1H, J=8.8 Hz, Ar—H), 6.39 (d, 1H, J=2.9 Hz, Ar—H), 6.39 (dd, 1H, J1=2.9 Hz, J2=8.8 Hz, Ar—H), 3.70 (s, 3H, —OCH3), 3.64 (s, 3H, —OCH3).

Aufarbeitung

  1. customthe mixture was evaporated
  2. customThe aqueous layer was separated
  3. extractionthe product was extracted with CH2Cl2 (2×100 mL)
  4. customThe combined extracts were dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2e679a0e713142a9972f56f4e1b6cdb6
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812040B2

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