4-Chloro-2-methoxybenzaldehyde → 1-(4-Chloro-2-methoxyphenyl)propan-1-one

HRID 272693

Reaction equation

HRID 272693 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH3:12][CH2:13][Mg+].[Br-].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[O:7])[CH2:12][CH3:13])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 138651154-Chloro-2-methoxybenzaldehydeHCID 178418287HCID 178418287, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 199011951-(4-Chloro-2-methoxyphenyl)propan-1-oneYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-methoxy-benzaldehyde (0.54 g, 3.2 mmol) in 10 mL of THF was treated with 3.0 M EtMgBr (2 mL, 6.0 mmol) at room temperature. The solution was stirred for 1 hour and quenched with MeOH. The solution was poured into water, treated 10 mL of 10% HCl, extracted with EtOAc several times. The combined organic layers were washed brine, dried (MgSO4), filtered, and concentrated. The residue was diluted with CH2Cl2, treated with PCC (1.33 g, 6.4 mmol) for 2 hours. The reaction mixture was filtered through a pack of silica gel to give 0.42 g of the title compound. MS (DCI) m/e 199 (M+H)+.

Workup

  1. customquenched with MeOH
  2. additionThe solution was poured into water
  3. additiontreated 10 mL of 10% HCl
  4. extractionextracted with EtOAc several times
  5. washThe combined organic layers were washed brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue was diluted with CH2Cl2
  10. filtrationThe reaction mixture was filtered through a pack of silica gel

Sources & evidence

ORD record
ord-255ec494d5f245e1888e65ce9141fd9c
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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