Acetophenone → Acetophenone

HRID 620968Notes

Reaction equation

HRID 620968 reaction equation
[Mg].[Br-].[CH:3]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[CH2:4].C(C1C=C([Mg]Br)C=CC=1)=C.[C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH3:22].[Cl-].[NH4+]>O1CCCC1>[CH:3]([C:5]1[CH:10]=[C:9]([C:21]([OH:23])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:22])[CH:8]=[CH:7][CH:6]=1)=[CH2:4].[C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH3:22]

Participants

8

Reactant 5

HCID 7410Acetophenone2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 187634923-Vinylbenzene bromideHCID 178436337HCID 178436337, compound2×

Product 2

HCID 7410AcetophenoneHCID 144235741-(3-Vinylphenyl)-1-phenylethyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 2 liter three-neck flask equipped with a dropping funnel, a reflux condenser and a stirrer was added 25.5 g (1.05 mole) of metallic magnesium and it was dried sufficiently by supplying dry nitrogen gas. After that, 50 ml of tetrahydrofuran which had been dried with a molecular sieve 5 A, was put into the flask and the contents were stirred vigorously. A solution of 183 g (1.0 mole) of 3-vinylbenzene bromide in 500 ml of dried tetrahydrofuran was dropped little by little over 2 hours. The reaction temperature was maintained at 75° to 80° C. and, after the addition of the solution, the stirring was continued for further 1 hour as it stands. Into the thus obtained Grignard reagent of 3-vinylphenylmagnesium bromide (formula VII), a solution of 122.6 g (1.02 mole) of acetophenone (formula VIII) in 500 ml of dried tetrahydrofuran was dropped little by little for 2 hours. The reaction temperature was maintained at 75° to 80° C. and, after the dropping, the stirring was continued for further 1 hour as it stands. The reaction mixture was then poured into 3 liter of an aqueous solution of 75 g of ammonium chloride and it was left to stand still for 20 hours and an oily layer was recovered to obtain 1-(3-vinylphenyl)-1-phenylethyl alcohol (VPA: formula V) in a yield of 89% (acetophenone basis) by distilling off the tetrahydrofuran.

Workup

  1. customTo a 2 liter three-neck flask equipped with a dropping funnel, a reflux condenser and a stirrer
  2. customwas dried sufficiently
  3. dry with materialAfter that, 50 ml of tetrahydrofuran which had been dried with a molecular sieve 5 A
  4. temperatureThe reaction temperature was maintained at 75° to 80° C.
  5. additionafter the addition of the solution
  6. temperatureThe reaction temperature was maintained at 75° to 80° C.
  7. waitafter the dropping, the stirring was continued for further 1 hour as it
  8. waitwas left
  9. waitto stand still for 20 hours
  10. customan oily layer was recovered

Sources & evidence

ORD record
ord-c161812c76144b4aad728a1cd8aec711
Source dataset
uspto-grants-1989_04
Patent number
US04822934

Reaction notes

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