2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

HRID 989285Notes

Reaction equation

HRID 989285 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F-].[K+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[CH2:13]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 7503Benzyl ChlorideHCID 522689Potassium Fluoride

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,4-dihydroxybenzaldehyde (20 g, 0.144 mol), potassium flouride (16.7 g, 2 equivalents) and benzyl chloride (29 mL, 1.75 equivalents) in acetonitrile (150 mL) is heated at reflux temperature for 16 hr, cooled to room temperature, concentrated, diluted with water and extracted with EtOAc. The combined extracts are dried over MgSO4 and concentrated in vacuo to give an oil residue. The residue is chromatographed (silica gel/10% EtOAc in hexanes to 50% EtOAc in hexanes as gradient eluents) to give the title product as a white solid, 25.9 g, identified by NMR and mass spectral analyses.

Workup

  1. temperatureat reflux temperature for 16 hr
  2. concentrationconcentrated
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts are dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give an oil residue
  8. customThe residue is chromatographed (silica gel/10% EtOAc in hexanes to 50% EtOAc in hexanes as gradient eluents)

Sources & evidence

ORD record
ord-a3b3afc8ea6f40299d8a7ae998438b1c
Source dataset
uspto-grants-2003_10
Patent number
US06638972B2

Reaction notes

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