Pyridine → 3-(2-Ethoxyphenoxy)-1,2-propanediol

HRID 1493959

Reaction equation

HRID 1493959 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2].[CH2:11]1[O:13][CH:12]1[CH2:14][OH:15].N1C=CC=CC=1>C(O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH:12]([OH:13])[CH2:14][OH:15])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11164GlycidolHCID 667552-Ethoxyphenol

Product 1

HCID 688253-(2-Ethoxyphenoxy)-1,2-propanediolYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 41.5 g (0.3 mole) of 2-ethoxyphenol, 29.6 g (0.4 mole) of glycidol, 2 ml of pyridine and 150 ml of absolute ethanol was heated at reflux temperature for 18 hr. The mixture was concentrated to a thick oil that crystallized slowly over several days. The crude product was chromatographed on a silica gel column (1.2 kg) using increasing portions of acetone in methylene chloride to elute the product. The desired fractions were combined and concentrated to give a yellow oil that crystallized on standing. The solid was triturated with petroleum ether and the mixture filtered to obtain 41.8 g of solid. Recrystallization from carbon tetrachloride yielded 37.2 g (58%) of white solid, mp 64°-65° C.

Workup

  1. temperatureat reflux temperature for 18 hr
  2. concentrationThe mixture was concentrated to a thick oil that
  3. customcrystallized slowly over several days
  4. customThe crude product was chromatographed on a silica gel column (1.2 kg)
  5. temperatureusing increasing portions of acetone in methylene chloride
  6. washto elute the product
  7. concentrationconcentrated
  8. customto give a yellow oil that
  9. customcrystallized
  10. customThe solid was triturated with petroleum ether
  11. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-13826c36e45d4e4ca3565ce540c167c4
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Linked notes

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