4-Methylmorpholine → 4-Chloro-2-methoxybenzaldehyde

HRID 352835

Reaction equation

HRID 352835 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([O:10][CH3:11])[CH:3]=1.CN1CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 2

HCID 79724-MethylmorpholineHCID 35493934 Chloro-2-methoxybenzyl alcohol

Product 1

HCID 138651154-Chloro-2-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (80 ml) was dissolved (4-chloro-2-methoxyphenyl)methanol (3.69 g). Under ice cooling, molecular sieve 4A (4.57 g), N-methylmorpholine (2.81 g) and tetra-n-propylammonium perruthenate (420 mg) were added to the resulting solution, followed by stirring at room temperature for 2.5 hours. The reaction mixture was distilled under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane:ethyl acetate=9:1), whereby the title compound (3.07 g) was obtained as pale yellow oil.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customwas obtained as pale yellow oil

Sources & evidence

ORD record
ord-ad5fea9e0b5f4ceb8a3ddf1d9c72e567
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Linked notes

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