Isopropyl iodide → HCID 62116082, compound

HRID 518847Notes

Reaction equation

HRID 518847 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:20]([CH3:22])[CH3:21]>C(#N)C>[CH:20]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6])([CH3:22])[CH3:21]

Participants

5

Conditions

Temperature
70 °C

Procedure

3.0 g of 3-hydroxy-4-nitrobenzaldehyde, 30 ml of acetonitrile, 5.9 g of caesium carbonate and 4.1 ml of 2-iodopropane are successively introduced into a three-necked round-bottomed flask under argon. The reaction mixture is heated at 70° C. for 17 h. After cooling to ambient temperature, the mixture is filtered through a sintered glass filter and the filtrate is concentrated to dryness under reduced pressure. The residue is taken up in a mixture of 50 ml of ethyl acetate and 15 ml of water, and then separated by settling out. The aqueous phase is separated and the organic phase is washed with 10 ml of water. The organic phase is then dried over magnesium sulfate and then concentrated to dryness under reduced pressure, so as to obtain 3.6 g of 3-isopropoxy-4-nitrobenzaldehyde in the form of a dark brown liquid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe mixture is filtered through a sintered glass
  3. filtrationfilter
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure
  5. additionThe residue is taken up in a mixture of 50 ml of ethyl acetate and 15 ml of water
  6. customseparated
  7. customThe aqueous phase is separated
  8. washthe organic phase is washed with 10 ml of water
  9. dry with materialThe organic phase is then dried over magnesium sulfate
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f143b00ec639456d8f5cbda9500298b6
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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