3-Hydroxybenzaldehyde → HCID 10753946, compound

HRID 1708493Notes

Reaction equation

HRID 1708493 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10](=O)([O-])[O-].[K+].[K+].BrC[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[CH:26]1[C:27]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:25]=1[CH2:10][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 1378441-(Bromomethyl)naphthalene

Product 1

HCID 10753946HCID 10753946, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (2.44 g; 20 mmol) in DMF (50 ml) were added potassium carbonate (3.04 g; 22 mmol) and bromomethylnaphthalene (4.64 g; 21 mmol), and the resulting mixture was stirred at room temperature for 16 h. The mixture was then poured into water (200 ml) and extracted with ethyl acetate (100 ml). The extract was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography (silica gel; methylene chloride-ethyl acetate 19:1) to provide 5.1 g of 3-(2-naphthylmethoxy)benzaldehyde.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe extract was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (silica gel; methylene chloride-ethyl acetate 19:1)

Sources & evidence

ORD record
ord-7b3f6a347ef246549b4df5d3b68f6591
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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