p-Toluenesulfonic acid → Methyl 3,5-dihydroxy-4-methylbenzoate

HRID 555167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555167
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[CH3:13]C1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[CH3:11])[C:5]([O:7][CH3:13])=[O:6]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 27480453,5-Dihydroxy-4-methylbenzoic Acid

Produkt 1

HCID 11458051Methyl 3,5-dihydroxy-4-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3,5-Dihydroxy-4-methylbenzoic acid (5.0 g, 29.79 mmol, 1.0 eq) and PTSA (1.13 g, 5.94 mmol, 0.2 eq) were dissolved in 50 ml of methanol, and the mixture was heated to reflux for 6 h. Methanol was evaporated. The resultant solid was washed with 10% sodium bicarbonate solution. The aqueous solution was extracted thrice with ethyl acetate. The combined organic layer was dried over sodium sulphate and evaporated under vacuum. Yield: 5.25 g (96%). 1H NMR (400 MHz, DMSO-d6): δ 1.98 (s, 3H), 3.78 (s, 3H), 6.93 (s, 2H), 9.53 (s, 2H). LCMS: (ES+) m/z=183 (M+H) Method: Column: PHENOMENEX® Luna C18 (4.6×30) mm, 5 micron. Mphase A: 10% MeOH-90% H2O-10 mM NH4OAc. Mphase B: 90% MeOH-10% H2O-10 mM NH4OAc. Flow: 5 ml/min

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h
  3. customMethanol was evaporated
  4. washThe resultant solid was washed with 10% sodium bicarbonate solution
  5. extractionThe aqueous solution was extracted thrice with ethyl acetate
  6. dry with materialThe combined organic layer was dried over sodium sulphate
  7. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f13df86490824119ad650454f82e7374
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048887B2

Notizen zur Reaktion

Wird geladen…