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

HRID 495900

反応式

HRID 495900 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-abda2acb42854a239d47af03a4a83cee
出典データセット
uspto-grants-2005_09
特許番号
US06942980B1

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