Phloroglucinol → 1,3,5-tris(2-hydroxyethoxy)benzene

HRID 585023Notes

Reaction equation

HRID 585023 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].C1(=O)[O:14][CH2:13][CH2:12]O1>[Br-].C([N+](CC)(CC)CC)C.CN(C=O)C>[OH:2][CH2:1][CH2:3][O:2][C:1]1[CH:9]=[C:7]([O:8][CH2:6][CH2:4][OH:5])[CH:6]=[C:4]([O:5][CH2:12][CH2:13][OH:14])[CH:3]=1

Participants

5

Reactant 2

HCID 359PhloroglucinolHCID 7303Ethylene carbonate

Product 1

HCID 113228581,3,5-tris(2-hydroxyethoxy)benzeneYield 74.3%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of phloroglucinol (12.60 g, 0.10 mol), ethylene carbonate (35 g, 0.39 mol), and tetraethylammonium bromide (8 g, 0.04 mol) in DMF (20 ml,) was heated at 150° C. for 14 hr. After evaporating the solvent, the residue was purified on a silica gel chromatography column using a mixture of methylene chloride and acetonitrile: 1/1, 1/2, 1/3 and 1/4 as eluents to give 9.6 g of 1,3,5-tris(2-hydroxyethoxy)benzene (37% yield). The product was purified further by recrystallization from cold methylene chloride and THF to afford 5.5 g (21%). 1H NMR (DMSO-d6): δ 6.08 (s, aromatic protons, 3H), 4.83 (s, OH, 3H), 3.92 (t, —OCH2—, 6H), 3.69 (m, —CH2OH, 8H). 13C NMR (DMSO-d6): δ 160.54 (aromatic C—O—), 93.81 (aromatic C—H), 69.53 (—CH2O—), 59.55 (—CH2OH). FT-IR (KBr, m−1): 3255 (OH), 2947, 2371, 1596, 1462, 1377, 1167, 1071, 1024, 902, 745.

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was purified on a silica gel chromatography column
  3. additiona mixture of methylene chloride and acetonitrile

Sources & evidence

ORD record
ord-f4c26400424c40239884dc1996b38964
Source dataset
uspto-grants-2005_08
Patent number
US06929747B2

Reaction notes

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