Acetic Acid → 4,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 324192

Reaktionsgleichung

Reaktionsgleichung von HRID 324192
[C:1]([OH:4])(=O)[CH3:2].C(OC(=O)C)(=O)C.[CH3:12][C:13]1([CH3:23])[C:22]2[C:17](=[CH:18]C=C[CH:21]=2)[CH2:16][CH2:15][CH2:14]1>C1C=CC=CC=1.O>[CH3:12][C:13]1([CH3:23])[C:14]2[C:2](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:1](=[O:4])[CH2:21][CH2:22]1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 161371,1-Dimethyl-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-oneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 350 ml of glacial acetic acid and 170 ml of acetic anhydride was cooled to 0° C. and CrO3, 25.0 g (0.25 mol) carefully added in small portions. The resulting mixture was stirred for 30 minutes before 120 ml of benzene was added. 1,2,3,4-tetrahydro-1,1-dimethylnaphthalene was added slowly as a solution in 30 ml of benzene. Upon completing the addition the reaction was stirred for 4 hours at 0° C. The solution was diluted with H2O (200 ml) and extracted with Et2O (5×50 ml). The combined organic layers were washed with water, saturated aqueous NaCO3, and saturated aqueous NaCl, before being dried over MgSO4. Removal of the solvents under reduced pressure, and distillation afforded 16.0 g (74%) of the product as a pale-yellow oil, bp 93-96° C./0.3 mm Hg 1H NMR (CDCl3): δ 8.02 (1H, dd, J=1.3, 7.8 Hz), 7.53 (1H, m ), 7.42 (1H, d, J=7.9 Hz), 7.29 (1H, m), 2.74 (2H, t, J=6.8 Hz), 2.02 (2H, t, J=6.8 Hz), 1.40 (6H, s).

Aufarbeitung

  1. additionCrO3, 25.0 g (0.25 mol) carefully added in small portions
  2. additionwas added
  3. additionthe addition the reaction
  4. extractionextracted with Et2O (5×50 ml)
  5. washThe combined organic layers were washed with water, saturated aqueous NaCO3, and saturated aqueous NaCl
  6. dry with materialbefore being dried over MgSO4
  7. customRemoval of the solvents
  8. distillationunder reduced pressure, and distillation

Quellen und Nachweise

ORD-Eintrag
ord-879d5d5fea5949728f68d5aa77b89fce
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218128B1

Verknüpfte Notizen

Wird geladen…