4-Hydroxybenzaldehyde → p-(Octyloxy)benzaldehyde

HRID 2273806Notes

Reaction equation

HRID 2273806 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 g, 81.8 mmol), and K2CO3 (34.0 g, 0.25 mol) in DMF (150 mL) was heated to reflux for 8 hours and then cooled to room temperature. The reaction mixture was subsequently diluted in toluene. The organic layer was washed with HCl (10%), brine, and water. The solvent was concentrated in vacuo and the oil was purified by short silica gel plug (dichloromethane (DCM) in n-hexanes, 10%). Solvent was dried in vacuo to afford the product 4-octyloxy benzaldehyde as a slightly colored oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 hours
  3. washThe organic layer was washed with HCl (10%), brine, and water
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe oil was purified by short silica gel plug (dichloromethane (DCM) in n-hexanes, 10%)
  6. customSolvent was dried in vacuo

Sources & evidence

ORD record
ord-917879f66cc549a59439010e40660481
Source dataset
uspto-grants-2015_09
Patent number
US09126890B2

Reaction notes

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