Methyl morpholine oxide → 2-Chloro-5-(2-methoxyethoxy)benzaldehyde

HRID 337620Notes

Reaction equation

HRID 337620 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])[CH:6]=[CH:5][C:4]=1[Cl:14].C[N+]1([O-])CC[O:19]CC1>O1CCOCC1>[Cl:14][C:4]1[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:8][C:3]=1[CH:2]=[O:19]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 591775552-(Bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene

Product 1

HCID 866359132-Chloro-5-(2-methoxyethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(Bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene (1 eq.) from the previous step and NMO (3 eq.) were stirred in dioxane (0.3 M) at 90° C. for 6 h. The reaction mixture was then quenched with saturated aqueous sodium bicarbonate and extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed further with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-9836b0276b1f434da0163e66daed1ae6
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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