Ethanol → HCID 20271559, compound

HRID 485156Notes

Reaction equation

HRID 485156 reaction equation
[OH:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10][CH3:11])[C:5]([O:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-:17].[K+].[K+].[I-].[Na+].[CH2:24](O)[CH3:25]>>[CH:8]([C:7]1[C:6]([O:10][CH3:11])=[C:5]([O:12][CH2:13][CH2:14][CH3:15])[CH:4]=[CH:3][C:2]=1[O:1][CH2:7][CH2:2][CH2:3][CH2:4][C:16]([O:17][CH2:24][CH3:25])=[O:19])=[O:9]

Participants

5

Reactant 4

HCID 702EthanolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 20271540HCID 20271540, compound

Product 1

HCID 20271559HCID 20271559, compound

Procedure

6-Hydroxy-2-methoxy-3-n-propoxybenzaldehyde (5.25 g, 0.025 M), ethyl 5-brown pentanoate (3.96 ml, 0.025 M), anhydrous potassium carbonate (3.71 g). sodium iodide (0.15 g) and 95% 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-methoxy-4-n-propoxyphenoxy)pentanoate 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-9755db91dc844130ba5e6cf10de31e3e
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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