Methyl morpholine oxide → 2-(Benzyloxy)-6-methylbenzaldehyde

HRID 554547Notes

Reaction equation

HRID 554547 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](OC)[C:10]=1[CH2:17][OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:19])[C:10]=1[CH:17]=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 674586102-Benzyloxy-6-methoxybenzyl alcohol

Product 1

HCID 860935782-(Benzyloxy)-6-methylbenzaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, a solution of (2-benzyloxy-6-methoxyphenyl)-methanol (3.46 g, 15.16 mmol) and N-methylmorpholine N-oxide (NMO, 2.66 g, 22.73 mmol) in dichloromethane (10 mL) was cooled in a water bath and tetra-n-propyl-ammonium perruthenate (TPAP, 152 mg, 0.43 mmol) was added thereto. The reaction mixture was stirred at the same temperature for 1.75 hours, and then subjected to Celite filtration and the solvent was distilled under reduce pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)] to obtain the title compound (3.08 g, 90%).

Workup

  1. filtrationsubjected to Celite filtration
  2. distillationthe solvent was distilled
  3. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)]

Sources & evidence

ORD record
ord-5301c3acadd746fd828fffa2131945bd
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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