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

HRID 637390노트

반응식

HRID 637390 반응식
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

참가 물질

5

반응물 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13408689HCID 13408689, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5d98f531cc224ccaa0b631cacdd2b95d
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04556676

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