4-Hydroxybenzaldehyde → 4-(2-Methoxyethoxy)benzaldehyde

HRID 2214968Notes

Reaction equation

HRID 2214968 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[I-].[K+].CC(C)([O-])C.[K+].[CH3:18][O:19][CH2:20][CH2:21]Cl>CN(C=O)C>[CH3:18][O:19][CH2:20][CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 123162-Chloroethyl methyl etherHCID 23665647Potassium tert-butoxide

Product 1

HCID 64855604-(2-Methoxyethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

146.5 g (1.2 mol) of 4-hydroxybenzaldehyde are dissolved in DMF, and 20 g (0.12 mol) of potassium iodide, 134.6 g (1.2 mol) of potassium tert-butoxide and 170.2 g (1.8 mol) of 2-chloroethyl methyl ether are added. The reaction mixture is stirred at 80° C. for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure. The residue is taken up in 1 l of ethyl acetate and extracted with 0.5 l of 1N aqueous sodium hydroxide solution. The ethyl acetate phase is dried using magnesium sulphate and concentrated under reduced pressure. The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar). This gives 184.2 g (85% of theory) of product.

Workup

  1. concentrationFor work-up, the reaction mixture is concentrated under reduced pressure
  2. extractionextracted with 0.5 l of 1N aqueous sodium hydroxide solution
  3. dry with materialThe ethyl acetate phase is dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. concentrationafter concentration
  7. distillationis distilled under high vacuum (b.p.=100° C. at 0.45 mbar)

Sources & evidence

ORD record
ord-ceca3998d8a546c1a9ad185bb0a38d12
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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