2,3-Dimethoxybenzaldehyde → 1-(2,3-Dimethoxyphenyl)ethanol

HRID 1603921Notes

Reaction equation

HRID 1603921 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[CH3:13][Mg]Br>C(OCC)C>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]([OH:6])[CH3:13]

Participants

4

Reactant 2

HCID 665812,3-DimethoxybenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 132708731-(2,3-Dimethoxyphenyl)ethanolYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2,3-dimethoxybenzaldehyde (10.0 g, 60.2 mmol) in dry ethyl ether (100 ml) was added at 0° C. with a 3M solution of methylmagnesium bromide in ethyl ether (35 ml) and left under stirring at 0° C. for 0.5 h. Afterwards the reaction mixture was added with a diphasic mixture of ethyl ether and an ammonium chloride saturated solution, extracting the aqueous phase with ethyl ether. The organic extracts were dried and the solvent was evaporated off under reduced pressure, thereby obtaining 10.06 g of the title compound (92% yield).

Workup

  1. waitleft
  2. extractionan ammonium chloride saturated solution, extracting the aqueous phase with ethyl ether
  3. customThe organic extracts were dried
  4. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-a717c936a7ac49008a804e86032e9f27
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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