Benzene → 6-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene

HRID 324194

Reaktionsgleichung

Reaktionsgleichung von HRID 324194
O[C:2]1([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[C:5]([CH3:14])([CH3:13])[CH2:4][CH2:3]1.C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=3)[C:5]([CH3:14])([CH3:13])[CH2:4][CH:3]=2)=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 105454491,2,3,4-Tetrahydro-1-hydroxy-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene2×

Produkt 1

HCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A flask equipped with a Dean-Stark trap was charged with 3.4 g of (9.85 mmol) of 1,2,3,4-tetrahydro-1-hydroxy-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene (Compound C) and 40 ml of benzene. A catalytic amount of p-toluenesulfonic acid monohydrate was added and the resulting solution heated to reflux for 2 hours. Upon cooling to room temperature, Et2O was added and the solution washed with H2O, saturated aqueous NaHCO3, and saturated aqueous NaCl then dried over MgSO4. Removal of the solvents under reduced pressure, and column chromatography (100% hexane/silica gel) afforded the title compound as a colorless solid. 1H NMR (CDCl3): δ 7.32 (1H, dd, J=2.1, 8.2 Hz), 7.21 (5H, m), 7.15 (1H, d, J=2.1 Hz), 5.98 (1H, t, J=4.7 Hz), 2.40 (3H, s), 2.32 (2H, d, J=4.7 Hz), 1.30 (6H, s).

Aufarbeitung

  1. customA flask equipped with a Dean-Stark trap
  2. temperaturethe resulting solution heated
  3. temperatureto reflux for 2 hours
  4. washthe solution washed with H2O, saturated aqueous NaHCO3, and saturated aqueous NaCl
  5. dry with materialthen dried over MgSO4
  6. customRemoval of the solvents under reduced pressure, and column chromatography (100% hexane/silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-288cd4246ab54c1c8d2c867d6838b058
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218128B1

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