Methyl iodide → 3-Chloro-4-methoxybenzaldehyde

HRID 655457Notes

Reaction equation

HRID 655457 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[C:11]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 170223-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 786193-Chloro-4-methoxybenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-chloro-4-hydroxybenzaldehyde (2.9 g, 18.412 mmol) in DMF (30 mL) was added K2CO3 (7.6 g, 55.238 mmol). CH3I (7.80 g, 55.238 mmol) was then added slowly at RT under an inert atmosphere. After addition was completed, the reaction mixture was brought to 80° C. and stirred for 1 h. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain crude product. The crude material was purified via silica gel column chromatography to afford 3-chloro-4-methoxybenzaldehyde (2.78 g, 93%) as a yellow solid.

Workup

  1. additionAfter addition
  2. customwas brought to 80° C.
  3. customThe reaction mixture was quenched with water (20 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain crude product
  10. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-b1674f508b144a17a141eccbcb913412
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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