1-Phenyl-1-propanone → 1-(2-Methylphenyl)-1-phenyl-1-propanol

HRID 566538Notes

Reaction equation

HRID 566538 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Mg]Cl.C1COCC1.[Cl-].[NH4+]>C(OCC)C>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([OH:4])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 71481-Phenyl-1-propanoneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178424304HCID 178424304, compound

Product 1

HCID 212663251-(2-Methylphenyl)-1-phenyl-1-propanolYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Propiophenone (6.7 g, 50 mmol) was added dropwise to a solution of 2-methylphenylmagnesium chloride (30 ml of a 2.0 M solution in diethyl ether) and dry THF (50 ml) under a nitrogen atmosphere. When the addition was complete the reaction mixture was heated at reflux temperature for 5 h. Excess of a saturated ammonium chloride solution was added and the mixture was extracted with diethyl ether (2×100 ml). The combined organic extracts were dried over potassium carbonate and the solvent was evaporated in vacuo to give 10.4 g (92%) of 1-(2-methyl phenyl)-1-phenyl-1-propanol.

Workup

  1. additionWhen the addition
  2. temperaturewas heated
  3. temperatureat reflux temperature for 5 h
  4. extractionthe mixture was extracted with diethyl ether (2×100 ml)
  5. dry with materialThe combined organic extracts were dried over potassium carbonate
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4cb7e0da3b0c480489149f974adbc8cb
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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