Phosphoric Acid → 2,4-Dimethylresorcinol

HRID 4885

Reaktionsgleichung

Reaktionsgleichung von HRID 4885
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.P(=O)(O)(O)O>[Pd].C(O)(C)C>[CH3:10][C:9]1[C:2]([OH:1])=[C:3]([CH3:4])[CH:6]=[CH:7][C:8]=1[OH:11]

Komponenten

5

Edukt 2

HCID 1004Phosphoric AcidHCID 803952,4-Dihydroxy-3-methylbenzaldehyde

Produkt 1

HCID 694522,4-DimethylresorcinolAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 2,4-dihydroxy-3-methylbenzaldehyde (30.0 g, 197 mmol) with isopropanol (3 L) was ice-cooled in a 5 L 3-neck flask fitted with a magnetic stirrer. Phosphoric acid (4 mL) and d10% palladium on carbon were added and the solution was sparged with nitrogen, then hydrogen. When uptake was judged to be complete (c. 1.5 hour) the solution was again sparged with nitrogen and then filtered through Celite®. The solvent was stripped off, the residue taken up in ethyl acetate, and the resulting solution washed with water (4×100 mL). The water washes were back-extracted with ethyl acetate and the combined organic layers dried over sodium sulfate and stripped down. Sublimation (95°, 0.05 torr) afforded a colorless solid (19.6 g, 72%). M.p. 107°-8° C. (Lit. 108°-109° C. [W. Baker et al., J. Chem. Soc., 2834-5 (1949).]). NMR (DMSO-d6): δ 1.969 (s, 3H), 2.037 (s, 3H), 6.220 (d, J=8.1 hz, 1H), 6.637 (d, J=8.1 hz, 1H), 7.929 (s, 1H), and 8.785 (s, 1H).

Aufarbeitung

  1. temperaturecooled in a 5 L 3-neck flask
  2. customfitted with a magnetic stirrer
  3. customthe solution was sparged with nitrogen
  4. custom(c. 1.5 hour)
  5. customwas again sparged with nitrogen
  6. filtrationfiltered through Celite®
  7. washthe resulting solution washed with water (4×100 mL)
  8. extractionThe water washes were back-extracted with ethyl acetate
  9. dry with materialthe combined organic layers dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-acac41327ddf4baf83b59f70db7ade15
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242796

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