4-Hydroxybenzaldehyde → Benzaldehyde, 4-(heptyloxy)-

HRID 2292437Notes

Reaction equation

HRID 2292437 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].O>CC(C)=O>[CH2:17]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 123691-Bromoheptane

Product 1

HCID 119740Benzaldehyde, 4-(heptyloxy)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Anhydrous potassium carbonate (55.5 g, 0.4 mol) was added to a stirred solution of 4-hydroxybenzaldehyde (24.5 g, 0.2 mol) in acetone (300 cm3), over a period of 30 min at room temperature. 1-Bromoheptane (40.3 g, 0.225 mol) was added dropwise and the resulting mixture heated under reflux (12 h). The solution was poured into water (1000 cm3), the product extracted into diethyl ether (2×300 cm3), and the combined ethereal extracts dried (MgSO4). The solvent was removed in vacuo and the product isolated as a colourless oil by distillation under reduced pressure.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux (12 h)
  3. extractionthe product extracted into diethyl ether (2×300 cm3)
  4. dry with materialthe combined ethereal extracts dried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe product isolated as a colourless oil by distillation under reduced pressure

Sources & evidence

ORD record
ord-8d12d91912b74cd8b4fb89b928b4b078
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

Loading…