Hydrochloric Acid → 1-(3-Methoxyphenyl)-1-(2-methylphenyl)-1-propanol

HRID 1614816

반응식

HRID 1614816 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Mg]Br.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:18](=[O:21])[CH2:19][CH3:20])[CH:15]=[CH:16][CH:17]=1.[Cl-].[NH4+].Cl>C1COCC1.O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:18]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])([OH:21])[CH2:19][CH3:20])[CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 5847653'-MethoxypropiophenoneHCID 178424303HCID 178424303, 화합물

생성물 1

HCID 212662911-(3-Methoxyphenyl)-1-(2-methylphenyl)-1-propanol수율 438.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2-methylphenyl magnesium bromide (prepared from 4.9 g magnesium turnings and 24 ml of 2-bromotoluene) in dry THF (300 ml) was added dropwise a solution of 3'-methoxypropiophenone (25.9 g, 0.16 mol) in dry THF (200 ml). When addition was complete the mixture was heated at reflux temperature for 2 h. Water (250 ml) was added followed by a saturated ammonium chloride solution (250 ml) and the mixture was left overnight. A 4 N hydrochloric acid solution was added until a clear solution was obtained and the phases was separated. The organic phase was dried over magnesium sulphate and the solvent evaporated in vacuo. The residue was submitted to flash chromatography on silica gel (690 g) using a gradient of n-heptane in ethyl acetate to give 28.2 g (55%) of 1-(3-methoxyphenyl)-1-(2-methylphenyl)-1-propanol. A mixture of 1-(3-methoxyphenyl)-1-(2-methylphenyl)-1-propanol (26.2 g, 0.10 mol), isopropanol (300 ml) and a 6 N solution of sulphuric acid (150 ml) was stirred at room temperature for 2 h. The reaction mixture was neutralised with a 4 N sodium hydroxide solution and extracted with ethyl acetate (2×200 ml). The combined organic phases was dried over magnesium sulphate and the solvent was evaporated in vacuo. The residue was submitted to flash chromatography on silica gel (800 g) using n-heptane as eluent to give 18.4 g (76%) of 1-(3-methoxyphenyl)-1-(2-methylphenyl)-1-propene.

후처리

  1. additionWhen addition
  2. temperaturewas heated
  3. temperatureat reflux temperature for 2 h
  4. customwas obtained
  5. customthe phases was separated
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-c53928a727ca4fc8bcc9618e9842793e
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198451

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