Sulfuric Acid → 1-(2-Methylphenyl)-1-phenyl-1-propene

HRID 566539Notes

Reaction equation

HRID 566539 reaction equation
CCCCCCC.C1COCC1.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(O)[CH2:21][CH3:22].C(O)(C)C.S(=O)(=O)(O)O>O>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:21][CH3:22]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 21263495Tetrahydrofuran heptaneHCID 212663251-(2-Methylphenyl)-1-phenyl-1-propanol

Product 1

HCID 544424051-(2-Methylphenyl)-1-phenyl-1-propeneYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TLC: rf=0.50 (SiO2; n-heptane/THF=7:3). 1-(2-Methylphenyl)-1-phenyl-1-propanol (10.4 g, 46 mmol) was dissolved into isopropanol (100 ml) and a 4 N sulphuric acid solution (50 ml) was added. The reaction mixture was heated at reflux temperature for 18 h and cooled to room temperature. Water (300 ml) was added and the mixture was extracted with dichloromethane (2×200 ml). The combined organic extracts was washed with a diluted sodium bicarbonate solution, dried (Na2SO4) and the solvent evaporated in vacuo to give 9.0 g (91%) of 1-(2-methylphenyl)-1-phenyl-1-propene. To a solution of 1-(2-methylphenyl)-1-phenyl-1-propene (9.0 g, 43 mmol) in carbon-tetrachloride (40 ml), N-bromosuccinimide (7.7 g, 43 mmol) and benzoylperoxide (0.1 g) were added. The reaction mixture was heated at reflux temperature for 18 h. The cooled reaction mixture was filtered through silica gel and the solvent evaporated in vacuo to give 9.3 g (76 %) of 3-bromo-1 (2-methylphenyl)-1-phenyl-1-propene.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 18 h
  3. extractionthe mixture was extracted with dichloromethane (2×200 ml)
  4. washThe combined organic extracts was washed with a diluted sodium bicarbonate solution
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e59733e743494826889965f2f44f4f3e
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

Loading…