Sodium Iodide → HCID 13092094, compound

HRID 485167Notes

Reaction equation

HRID 485167 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2].Br[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[C:1]([NH:4][C:5]1[C:6]([CH:7]=[O:8])=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 20271536HCID 20271536, compound

Product 1

HCID 13092094HCID 13092094, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetylamino-6-hydroxybenzaldehyde (0.895 g, 0.005 M), ethyl 5-bromopentanoate (1.05 g. 0.005 M), anhydrous potassium carbonate (0.76 g), sodium iodide (50 mg) and 95% ethanol (20 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 M sodium hydroxide solution, water, dried (sodium sulphate) and evaporated. The residue (ethyl 5-(3-acetylamino-2-formylphenoxy)pentanoate) was dissolved in 95% ethanol (20 ml) and treated with stirring over 1 hr with 1 N sodium hydroxide (4.5 ml), and then stirred at room temperature (2 hours). The solution was evaporated to one-third volume, diluted with water (10 ml) and acidified with concentrated hydrochloric acid with cooling. The precipitated solid was filtered off, washed well with water and recrystallised from benzene/petrol (charcoal) to give 5-(3-acetylamino- 2-formylphenoxy)pentanoic acid, m.p. 119°-121° C. (Found: C, 60.55; H, 6.26; N, 4.88%. C14H17NO5 requires C, 60.22; H, 6.09; N, 5.02%).

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 M sodium hydroxide solution, water
  8. dry with materialdried (sodium sulphate)
  9. customevaporated
  10. dissolutionThe residue (ethyl 5-(3-acetylamino-2-formylphenoxy)pentanoate) was dissolved in 95% ethanol (20 ml)
  11. additiontreated
  12. stirringwith stirring over 1 hr with 1 N sodium hydroxide (4.5 ml)
  13. stirringstirred at room temperature (2 hours)
  14. customThe solution was evaporated to one-third volume
  15. additiondiluted with water (10 ml)
  16. temperaturewith cooling
  17. filtrationThe precipitated solid was filtered off
  18. washwashed well with water
  19. customrecrystallised from benzene/petrol (charcoal)

Sources & evidence

ORD record
ord-cef1570af21b46df91816e084368c0b4
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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