Water → Naphthalene, 1,2-dihydro-4-(4-methoxyphenyl)-

HRID 637390ノート

反応式

HRID 637390 の反応式
O[C:2]1([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][CH2:4][CH:3]=2)=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13408689HCID 13408689、化合物

生成物 1

HCID 12048655Naphthalene, 1,2-dihydro-4-(4-methoxyphenyl)-収率 67%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 1-hydroxy-1-(4-methoxyphenyl)-tetralin (18 g., 0.071 mole) in toluene (250 ml.) was treated with para-toluenesulfonic acid (5 mg.) and the resulting solution stirred at reflux for 16 hours, with complete water removal accomplished by means of a Dean-Stark trap. The reaction mixture was then cooled to room temperature, washed sequentially with 10% aqueous sodium bicarbonate solution (100 ml.), water (100 ml.) and saturated aqueous sodium chloride solution (100 ml.), dried (MgSO4) and evaporated under vacuum to an oil, which was purified by silica gel chromatography (elution with a hexane-toluene gradient) to give 12 g. of the named compound (67% yield, oil).

後処理

  1. washwashed sequentially with 10% aqueous sodium bicarbonate solution (100 ml.), water (100 ml.) and saturated aqueous sodium chloride solution (100 ml.)
  2. dry with materialdried (MgSO4)
  3. customevaporated under vacuum to an oil, which
  4. customwas purified by silica gel chromatography (
  5. washelution with a hexane-toluene gradient)
  6. customto give 12 g

出典と根拠

ORDレコード
ord-5d98f531cc224ccaa0b631cacdd2b95d
出典データセット
uspto-grants-1985_12
特許番号
US04556676

反応ノート

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