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

HRID 1614816

Reaction equation

HRID 1614816 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c53928a727ca4fc8bcc9618e9842793e
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Linked notes

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