1,3-Diacetoxy-2,4-dimethylbenzene → 2,4-Dimethylresorcinol

HRID 1003622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003622
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([O:18]C(=O)C)[C:12]=1[CH3:22])(=O)C>CCOCC>[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([OH:18])[C:12]=1[CH3:22]

Komponenten

4

Edukt 2

HCID 211865741,3-Diacetoxy-2,4-dimethylbenzeneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 694522,4-DimethylresorcinolAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a slurry of lithium aluminum hydride (0.56 g, 14.76 mmol) in ether (35 mL) was added 1,3-diacetoxy-2,4-dimethylbenzene (the compound of Preparation 24, 1.65 g, 7.42 mmol in 40 mL of ether) via syringe. The mixture was stirred overnight; then it was carefully quenched with sodium sulfate decahydrate (excess). The mixture was dried with anhydrous sodium sulfate, filtered, and concentrated to give 0.62 g (62%) of 1,3-dihydroxy-2,4-dimethylbenzene as a waxy light yellow solid which had: NMR δ 6.83 (d, J=8 Hz, 1 H), 6.34 (d, J=8.1 Hz, 1 H), 4.71 (s, 2 H), 2.19 (s, 3 H), 2.17 (s, 3 H). There was also a small amount of an impurity observed in the NMR spectrum but the product was found to be suitable for use without further purification. The product was somewhat air sensitive and was used the same day it was synthesized.

Aufarbeitung

  1. customthen it was carefully quenched with sodium sulfate decahydrate (excess)
  2. dry with materialThe mixture was dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6f8864b0b3b045f4b437d0aeb89b552e
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046213

Notizen zur Reaktion

Wird geladen…