2-Methoxy-5-(trifluoromethoxy)benzaldehyde → 1-[2-Methoxy-5-(trifluoromethoxy)phenyl]ethan-1-ol

HRID 1267888Notes

Reaction equation

HRID 1267888 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:4]=1[CH:5]=[O:6].[CH3:16][Mg]Br>O1CCCC1>[OH:6][CH:5]([C:4]1[CH:7]=[C:8]([O:11][C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[CH3:16]

Participants

4

Reactant 2

HCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 185425151-[2-Methoxy-5-(trifluoromethoxy)phenyl]ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 2-methoxy-5-(trifluoromethoxy)benzaldehyde (1.0 g, 4.5 mmol) in tetrahydrofuran (10 mL) at 0° C. was added a solution of methyl magnesium bromide in tetrahydrofuran (1.6 mL, 3M, 4.7 mmol). The solution was then warmed to room temperature and quenched with saturated aqueous ammonium chloride solution (50 mL). The suspension formed was extracted with ethyl acetate (2×100 mL) and the extracts were dried (MgSO4). Concentration in vacuo yielded the title compound as an oil (1.03 g, 4.4 mmol).

Workup

  1. customquenched with saturated aqueous ammonium chloride solution (50 mL)
  2. customThe suspension formed
  3. extractionwas extracted with ethyl acetate (2×100 mL)
  4. dry with materialthe extracts were dried (MgSO4)
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-65aaebd2529f4c77b55bad4fccef33e4
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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