Water → 1,1-Diphenylpropan-1-ol

HRID 566534Notes

Reaction equation

HRID 566534 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+].O>C(OCC)C>[C:5]1([C:1]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([OH:4])[CH2:2][CH3:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 71481-Phenyl-1-propanoneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 2261491,1-Diphenylpropan-1-olYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a well-stirred solution of propiophenone (20.1 g, 0.15 mol) in dry diethyl ether (125 ml) kept under nitrogen at room temperature was added a solution of phenylmagnesium bromide (55 ml, 3 M in diethyl ether) in dry diethyl ether (25 ml). The reaction mixture was stirred for 1 h and a mixture of a saturated ammonium chloride solution (100 ml) and water (50 ml) was added. The phases were separated and the aqueous phase was extracted with diethyl ether (100 ml). The combined organic phases was washed with a 0.5 N hydrochloric acid solution and dried (Na2SO4). The solvent was evaporated in vacuo to give a solid residue which was triturated with cyclohexane (100 ml). The solid was collected by filtration and dried to give 26.4 g (83%) of 1,1-diphenyl-1-propanol.

Workup

  1. customkept under nitrogen at room temperature
  2. additionwas added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with diethyl ether (100 ml)
  5. washThe combined organic phases was washed with a 0.5 N hydrochloric acid solution
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated in vacuo
  8. customto give a solid residue which
  9. customwas triturated with cyclohexane (100 ml)
  10. filtrationThe solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-3a1128edae844c199fa63c85b4b0aeda
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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