Ammonia → 2-(3-methoxyphenyl)-2-propanol

HRID 1373252Notes

Reaction equation

HRID 1373252 reaction equation
Br[CH2:2][Mg].[CH3:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=[O:6].N>C(OCC)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([C:5]([OH:6])([CH3:2])[CH3:4])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 114603-MethoxyacetophenoneHCID 178507037HCID 178507037, compound

Product 1

HCID 5904222-(3-methoxyphenyl)-2-propanolYield 98.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromomethylmagnesium (3 M diethyl ether solution) (24 ml, 72 mmols) was dropwise added to a diethyl ether (200 ml) solution of 3-methoxyacetophenone (10 g, 67 mmols) at room temperature. After the addition, the mixture was stirred at room temperature for 1 hour. Saturated aqueous ammonia was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with brine, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure to give an oil of 2-(3-methoxyphenyl)propan-2-ol (11 g, 98%).

Workup

  1. additionAfter the addition
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c037fcf82871461ebfc0917c3f27b85b
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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