1-Bromooctane → HCID 43128598, compound

HRID 2174399Notes

Reaction equation

HRID 2174399 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:14]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 181694-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 43128598HCID 43128598, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxy-3-nitrobenzaldehyde (10.0 g, 81.8 mmol), 1-bromooctane (15.8 mmol, 81.8 mmol), and K2CO3 (34.0 g, 0.25 mol) in DMF (150 mL) was heated to reflux for hours. After cooling the reaction back down to room temperature, the reaction mixture was diluted in toluene and the organic layer was washed with 10% HCl, brine, and water. After concentrating in vacuo, the oil was purified by short silica gel plug (10% DCM in n-hexanes). Solvent was dried in vacuo to afford the 4-octyloxy-3-nitrobenzaldehyde as a slightly colored oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for hours
  3. temperatureAfter cooling
  4. customthe reaction back down to room temperature
  5. washthe organic layer was washed with 10% HCl, brine, and water
  6. concentrationAfter concentrating in vacuo
  7. customthe oil was purified by short silica gel plug (10% DCM in n-hexanes)
  8. customSolvent was dried in vacuo

Sources & evidence

ORD record
ord-00315370a7034c38b72fdadec1b65643
Source dataset
uspto-grants-2015_06
Patent number
US09061965B2

Reaction notes

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