4-Chlorophenol → 4-(4-Chlorophenoxy)benzaldehyde

HRID 1653833Notes

Reaction equation

HRID 1653833 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O-:10].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:2]2[CH:7]=[CH:6][C:5]([CH:9]=[O:10])=[CH:4][CH:3]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 46844-ChlorophenolHCID 10942334Sodium Methoxide

Product 1

HCID 38517644-(4-Chlorophenoxy)benzaldehydeYield 127.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chlorophenol (22.6 g) was added to a stirred solution of sodium methoxide (9.5 g) in methanol (80 ml). After 30 min the solvent was evaporated in vacuo. Residual traces of methanol were removed by addition of toluene and evaporating again in vacuo. The residue was taken up in DMF (200 ml) and 4-fluorobenzaldehyde (19.85 g) added. The mixture was stirred and heated at 120° for 4 hr, cooled, poured into water and extracted with toluene (2×200 ml). The combined extracts were washed with water, 2M sodium hydroxide and satd. brine, dried over magnesium sulphate and concentrated to leave a brown oil. Distillation gave the title compound (26.03 g), b.p.=140°-50°/0.5 mm.

Workup

  1. customAfter 30 min the solvent was evaporated in vacuo
  2. customwere removed by addition of toluene
  3. customevaporating again in vacuo
  4. addition4-fluorobenzaldehyde (19.85 g) added
  5. temperatureheated at 120° for 4 hr
  6. temperaturecooled
  7. additionpoured into water
  8. extractionextracted with toluene (2×200 ml)
  9. washThe combined extracts were washed with water, 2M sodium hydroxide and satd
  10. dry with materialbrine, dried over magnesium sulphate
  11. concentrationconcentrated
  12. customto leave a brown oil
  13. distillationDistillation

Sources & evidence

ORD record
ord-03ef9b4c14f64946b5835a195bd93f32
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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