Sulfuric Acid → 1-(3-Methoxyphenyl)-1-(2-methylphenyl)-1-propene

HRID 566546Notes

Reaction equation

HRID 566546 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])(O)[CH2:10][CH3:11])[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:10][CH3:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 212662911-(3-Methoxyphenyl)-1-(2-methylphenyl)-1-propanol

Product 1

HCID 542515281-(3-Methoxyphenyl)-1-(2-methylphenyl)-1-propeneYield 77.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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 (MgSO4) 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-methoxy-phenyl)-1-(2-methylphenyl)-1-propene.

Workup

  1. extractionextracted with ethyl acetate (2×200 ml)
  2. dry with materialThe combined organic phases was dried (MgSO4)
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-93b58251250b44cf8cce0c3e3a775ccc
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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