4-Hydroxybenzaldehyde → p-Dodecyloxybenzaldehyde

HRID 1243264Notes

Reaction equation

HRID 1243264 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:2]([O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Product 1

HCID 141069p-DodecyloxybenzaldehydeYield 67.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-bromododecane (43.5 g, 0.22 mol), 4-hydroxybenzaldehyde (25 g, 0.20 mol), potassium carbonate (69 g, 0.5 mol) and butanone (500 cm3) was heated under reflux for 24 hours. The cooled solution was filtered and the filtrate evaporated down under reduced pressure. The crude product was then distilled at 142° [email protected] mmHg, to give a liquid, which crystallised on cooling to yield 39.2 g (67.6%) of a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe cooled solution was filtered
  4. customthe filtrate evaporated down under reduced pressure
  5. distillationThe crude product was then distilled at 142° [email protected] mmHg
  6. customto give a liquid, which
  7. customcrystallised
  8. temperatureon cooling

Sources & evidence

ORD record
ord-a28a00a7c91f4a6383c05da965304d40
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

Loading…