4-Hydroxybenzaldehyde → 4-(Pyridin-2-ylmethoxy)benzaldehyde

HRID 1891931Notes

Reaction equation

HRID 1891931 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23393Picolyl chloride

Product 1

HCID 7596674-(Pyridin-2-ylmethoxy)benzaldehydeYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide (250 mL) solution of 4-hydroxybenzaldehyde (20 g, 164 mmol) and 2-picolyl chloride (27 g, 165 mmol) was added potassium carbonate (68 g, 492 mmol), which was stirred for 3 days at room temperature. This mixture was partitoned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (29 g, 83%). The title compound was not purified but used for the next reaction.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-1f8e685b4d394e0bbe27fbbc584b1953
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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