3-Hydroxyacetophenone → 3-(2-Hydroxypropan-2-yl)phenol

HRID 2066390Notes

Reaction equation

HRID 2066390 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:11][Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[OH:10][C:8]([C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=1)([CH3:11])[CH3:9]

Participants

6

Reactant 3

HCID 84873-HydroxyacetophenoneHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 4581423-(2-Hydroxypropan-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3′-Hydroxyacetophenone (500 mg) was dissolved in tetrahydrofuran (10 ml), and the solution was slowly added dropwise with a 3 M solution of methylmagnesium bromide in diethyl ether (3.7 ml) under ice cooling. The mixture was stirred at the same temperature for 2 hours, and then added with saturated aqueous ammonium chloride, 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=5:1 to 1:1) to obtain the title compound (224.3 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1 to 1:1)

Sources & evidence

ORD record
ord-39c07a8b5ee34016b3b834139786b5f3
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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