Potassium Iodide → HCID 13630976, compound

HRID 1981561Notes

Reaction equation

HRID 1981561 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Cl)(=[O:15])[CH3:14].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 1702851-Hexanol, 6-chloro-, 1-acetate

Product 1

HCID 13630976HCID 13630976, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 50 g (300 mmol) of 5-hydroxy-2-nitrobenzaldehyde, 59 g (330 mmol) 6-chlorohexanol acetate, 5 g of potassium iodide, and 50 g of potassium carbonate in 500 ml of dry DMF was heated to 100° C. under dry nitrogen for 3 h. The reaction was cooled, filtered and evaporated to a dark oil. The crude product was dissolved in 500 ml of ethyl acetate, and the organic layer was washed twice with 300 ml of saturated sodium carbonate, and twice with 300 ml of brine, dried filtered and evaporated. Distillation (180° C., 0.2 mm) gave a yellow oil which solidified on cooling, to yield 81.5 g (263 mmol, 88%) of 5-(6-acetoxyhexyl)oxy-2-nitrobenzaldehyde, m.p. 42°-43° C.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated to a dark oil
  4. dissolutionThe crude product was dissolved in 500 ml of ethyl acetate
  5. washthe organic layer was washed twice with 300 ml of saturated sodium carbonate
  6. dry with materialtwice with 300 ml of brine, dried
  7. filtrationfiltered
  8. customevaporated
  9. distillationDistillation (180° C., 0.2 mm)
  10. customgave a yellow oil which
  11. temperatureon cooling

Sources & evidence

ORD record
ord-8bfd1f2776ba4b10818822c6111e55f9
Source dataset
uspto-grants-1986_06
Patent number
US04593029

Reaction notes

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