Potassium Iodide → 2-Methyl-4-[(prop-2-en-1-yl)oxy]benzaldehyde

HRID 2113883Notes

Reaction equation

HRID 2113883 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([CH3:18])[CH:11]=1.[CH2:19](Br)[CH:20]=[CH2:21]>CC(=O)CC>[CH2:21]([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([CH3:18])[CH:11]=1)[CH:20]=[CH2:19]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 4581854-Hydroxy-2-methylbenzaldehyde

Product 1

HCID 222420922-Methyl-4-[(prop-2-en-1-yl)oxy]benzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
65 °C

Procedure

31.7 g (229 mmol) potassium carbonate and 9.51 g (57.3 mmol) potassium iodide were given to a solution of 15.6 g (115 mmol) 4-hydroxy-2-methyl-benzaldehyde and 55.4 g (458 mmol) allyl bromide in 500 ml 2-butanone and stirred for 16 h at 65° C. Solvents were distilled off and the residue distributed between ethyl acetate and 1 N sodium hydroxide. The organic layer was separated and the aqueous solution extracted once with ethyl acetate. The combined organic phases were dried and evaporated to give 19.8 g (98%) of 4-allyloxy-2-methyl-benzaldehyde.

Workup

  1. distillationSolvents were distilled off
  2. customThe organic layer was separated
  3. extractionthe aqueous solution extracted once with ethyl acetate
  4. customThe combined organic phases were dried
  5. customevaporated

Sources & evidence

ORD record
ord-70346f8839f748e3bd83f009e6f6d7a4
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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