반응 #705201

반응 방정식

p-toluenesulfonic acid monohydrate

1,2,3,4-tetrahydro-1-hydroxy-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene

Compound C

1,2,3,4-tetrahydro-1-hydroxy-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene

benzene

→

title compound

3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene

용매

Et2O

반응 조건

후처리

1. 1
   기타A flask equipped with a Dean-Stark trap
2. 2
   온도the resulting solution heated
3. 3
   온도to reflux for 2 hours
4. 4
   세척the solution washed with H2O, saturated aqueous NaHCO3, and saturated aqueous NaCl
5. 5
   건조then dried over MgSO4
6. 6
   기타Removal of the solvents under reduced pressure, and column chromatography (100% hexane/silica gel)

실험 절차

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).

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