3-Hydroxyacetophenone → HCID 67387533, compound

HRID 2066392Notes

Reaction equation

HRID 2066392 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+]>O1CCCC1>[OH:10][C:8]([C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9]

Participants

5

Reactant 3

HCID 84873-HydroxyacetophenoneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 67387533HCID 67387533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3′-Hydroxyacetophenone (5.0 g) was dissolved in tetrahydrofuran (100 ml), and the solution was added dropwise with a 1 M solution of phenylmagnesium bromide in tetrahydrofuran (100 ml) at −30° C. Then mixture was further added with tetrahydrofuran (100 ml), and the mixture was stirred for 3 hours with gradually warming it. The mixture was added with saturated aqueous ammonium chloride under ice cooling, the mixture was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to obtain the title compound (7.55 g).

Workup

  1. temperaturewith gradually warming it
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-f0db1c6c5ced43d1aef3cb5376bac90a
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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