4-Hydroxybenzaldehyde → HCID 18767026, compound

HRID 481263Notes

Reaction equation

HRID 481263 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH:15]([O:30][C:31](=[O:42])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]Br)[CH2:16][O:17][C:18](=[O:29])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)=[O:12].[OH:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=[O:49])=[CH:46][CH:45]=1.[C:52](=[O:55])([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH:48]([C:47]1[CH:50]=[CH:51][C:44]([O:43][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH:15]([O:30][C:31](=[O:42])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][O:43][C:44]2[CH:51]=[CH:50][C:47]([CH:52]=[O:55])=[CH:46][CH:45]=2)[CH2:16][O:17][C:18](=[O:29])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:43][C:44]2[CH:51]=[CH:50][C:47]([CH:48]=[O:49])=[CH:46][CH:45]=2)=[O:12])=[CH:45][CH:46]=1)=[O:49]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 18767010HCID 18767010, compound

Product 1

HCID 18767026HCID 18767026, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 10.0 g 1,2,3-tris(10-bromodecanoyloxy)propane, 4.6 g 4-hydroxybenzaldehyde, 52.4 g anhydrous potassium carbonate and 250 ml ethyl-methyl ketone is heated under gentle reflux overnight. The reaction mixture is filtered to remove inorganic material and the filtrate evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 8.1 g of 1,2,3-tris(10-[4formylphenoxy]decanoyloxy)propane.

Workup

  1. temperatureis heated
  2. temperatureunder gentle reflux overnight
  3. filtrationThe reaction mixture is filtered
  4. customto remove inorganic material
  5. customthe filtrate evaporated down
  6. customThe residue is purified by column chromatography on silica gel
  7. customrecrystallisation from acetonitrile

Sources & evidence

ORD record
ord-15aa882db8984ed0ba8793fa89c5f83d
Source dataset
uspto-grants-2003_11
Patent number
US06653499B1

Reaction notes

Loading…