Water → 1-Hydroxy-3-(4-methoxyphenyl)propan-2-one

HRID 1994307Notes

Reaction equation

HRID 1994307 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[OH2:12].[O-:13][Mn](=O)(=O)=O.[K+].C([O-])(O)=O.[Na+]>C(O)(=O)C.CC(C)=O>[OH:12][CH2:3][C:2](=[O:13])[CH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8815EstragoleHCID 516875Potassium PermanganateHCID 516892Sodium Bicarbonate

Product 1

HCID 134834241-Hydroxy-3-(4-methoxyphenyl)propan-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

4-Allylanisole (98%; 3.0 g; 19.86 mmol) was dissolved in glacial acetic acid (180 ml), water (180 ml) and acetone (180 ml). KMnO4 (4.7 g; 29.79 mmol) was added over the course of 1 h. The mixture was then stirred at (RT) for 1 h. It was then decolorized with saturated NaHCO3 solution. The reaction volume was reduced in a rotary evaporator. This was followed by extraction with CH2Cl2, washing of the organic phase with water and drying over Na2SO4. The solvent was then removed in a rotary evaporator. The oily residue was purified by column chromatography (SiO2; EtOAc/n-heptane 1:2). 1-Hydroxy-3-(4-methoxyphenyl)propan-2-one was obtained as a white crystalline powder. MS: 81.20 (M+H); Rt: 0.83 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. customThe reaction volume was reduced in a rotary evaporator
  2. extractionThis was followed by extraction with CH2Cl2
  3. washwashing of the organic phase with water
  4. dry with materialdrying over Na2SO4
  5. customThe solvent was then removed in a rotary evaporator
  6. customThe oily residue was purified by column chromatography (SiO2; EtOAc/n-heptane 1:2)

Sources & evidence

ORD record
ord-b7436b1b6d074df4a985ec51b32d11c9
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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