Diethyl Ether → 3-Methoxypropiophenone

HRID 566545

Reaction equation

HRID 566545 reaction equation
C([Mg]Br)C.CO[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#N.C1[CH2:19][O:18][CH2:17][CH2:16]1.[Cl-].[NH4+].C([O:24]CC)C>O>[CH3:19][O:18][CH2:17][CH2:16][C:10]([C:9]1[CH:8]=[CH:7][CH:14]=[CH:13][CH:12]=1)=[O:24]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 737123-MethoxybenzonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 109427883-MethoxypropiophenoneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of ethyl magnesium bromide in diethyl ether (58 ml, 3 M) was added dropwise at room temperature to a mixture of 3-methoxybenzonitrile (21.2 g, 0.159 mol) and dry THF (250 ml). When addition was complete the mixture was stirred for 1 h at room temperature, 3 h at 40° C. and finally stirred overnight at room temperature. Water (250 ml) was added followed by a saturated ammonium chloride solution (250 ml) and the mixture was stirred for 1 h at room temperature. The phases were separated and the aqueous phase was extracted with ethyl acetate (100 ml). The combined organic phases was dried (MgSO4) and the solvent evaporated in vacuo to give 25.9 g (99%) of 3-methoxypropiophenone.

Workup

  1. additionWhen addition
  2. stirringthe mixture was stirred for 1 h at room temperature
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (100 ml)
  5. dry with materialThe combined organic phases was dried (MgSO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-a25213fbab6145e6a7bf02aef9f90f80
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Linked notes

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