4-Hydroxybenzaldehyde → HCID 85792393, compound

HRID 985719Notes

Reaction equation

HRID 985719 reaction equation
[H-].[Na+].O[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17]Cl>CN(C)C=O>[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 85792393HCID 85792393, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2.4 g (60%), 60 mmol) was added to 4-hydroxybenzaldehyde (6.0 g, 50 mmol) in N, N-dimethylformamide (100 mL). The suspension was stirred for 1 hour and then treated with 2-methoxyethoxymethyl chloride (6.8 mL, 60 mmol), and allowed to stir an additional 16 hours. The reaction was then partitioned between water and ether:ethyl acetate (1:1). The organics were then washed with water (4×), dried (potassium carbonate), and concentrated. The crude materials were then purified by silica gel chromatography (hexanes:ethyl acetate) to afford the title compound (9.0 g).

Workup

  1. stirringto stir an additional 16 hours
  2. customThe reaction was then partitioned between water and ether:ethyl acetate (1:1)
  3. washThe organics were then washed with water (4×)
  4. dry with materialdried (potassium carbonate)
  5. concentrationconcentrated
  6. customThe crude materials were then purified by silica gel chromatography (hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-2baa790b87dc41be9312b4fc10d86f4b
Source dataset
uspto-grants-2005_03
Patent number
US06872834B2

Reaction notes

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