Sodium Iodide → (+/-)-Ethyl 5-(2-formyl-3-methoxyphenoxy)-2-methylpentanoate

HRID 647914

Reaction equation

HRID 647914 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].Br[CH2:13][CH2:14][CH2:15][CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[CH:4]([C:3]1[C:6]([O:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH2:13][CH2:14][CH2:15][CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 20484352Ethyl 5-bromo-2-methylpentanoate

Product 1

HCID 54476439(+/-)-Ethyl 5-(2-formyl-3-methoxyphenoxy)-2-methylpentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxy-6-methoxybenzaldehyde (3.74 g, 0.025 M), ethyl 5-bromo-2-methylpentanoate (5.58 g, 0.025 M), anhydrous potassium carbonate (3.72 g), sodium iodide (0.11 g) and ethanol (50 ml) were refluxed with stirring for 16 hr. The cooled reaction mixture was filtered and the solid washed well with ethanol. The filtrate was evaporated to dryness and the residue partitioned between ether and water. The organic layer was separated and washed with 2 N sodium hydroxide solution, water, dried (sodium sulphate) and evaporated to give (±)-ethyl 5-(2-formyl-3-methoxyphenoxy)-2-methylpentanoate, 5.3 g, 72%, as an oil.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe solid washed well with ethanol
  4. customThe filtrate was evaporated to dryness
  5. customthe residue partitioned between ether and water
  6. customThe organic layer was separated
  7. washwashed with 2 N sodium hydroxide solution, water
  8. dry with materialdried (sodium sulphate)
  9. customevaporated

Sources & evidence

ORD record
ord-dc1268eab54c499baf511a56a0b49ecf
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Linked notes

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