4-Hydroxybenzaldehyde → p-(Octyloxy)benzaldehyde

HRID 2174398Notes

Reaction equation

HRID 2174398 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 90358p-(Octyloxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (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 8 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 benzaldehyde as a slightly colored oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 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-83dc8c67da0f4adc85719f586b85ce32
Source dataset
uspto-grants-2015_06
Patent number
US09061965B2

Reaction notes

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