Methyl morpholine oxide → 4-(3-Hydroxypropoxy)benzaldehyde

HRID 2390531Notes

Reaction equation

HRID 2390531 reaction equation
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[OH:11][CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:12]=[CH:13][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 11458058Benzenemethanol, 4-(3-hydroxypropoxy)-

Product 1

HCID 113558464-(3-Hydroxypropoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of the above 3-(4-hydroxymethyl-phenoxy)-propan-1-ol (1.50 g, 8.23 mmol) in acetonitrile (25 mL) is added N-methylmorpholine-N-oxide (1.50 g, 12.38 mmol) followed by tetrapropylammonium perruthenate (140 mg, 0.43 mmol). The dark solution is stirred at rt for 2 h before the solvent is removed in vacuo. The crude product is purified by column chromatography on silica gel (heptane/EA) to give 4-(3-hydroxy-propoxy)-benzaldehyde. 1H NMR (D6-DMSO): δ 9.83 (s, 1H), 7.85-7.81 (m, 2H), 7.12-7.07 (m, 2H9, 4.56 (t, J=5.3 Hz, 1H), 4.14 (t, J=6.4 Hz, 2H), 3.57-3.51 (m, 2H), 1.88 (p, J=6, 4 Hz, 2H).

Workup

  1. customis removed in vacuo
  2. customThe crude product is purified by column chromatography on silica gel (heptane/EA)

Sources & evidence

ORD record
ord-cc38bfe282cf42d1a5349a4d6a0a740d
Source dataset
uspto-grants-2012_09
Patent number
US08273779B2

Reaction notes

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