Pyridine → 1,2-Propanediol, 3-((o-benzyloxy)phenoxy)-

HRID 1613729Notes

Reaction equation

HRID 1613729 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]1[O:18][CH:17]1[CH2:19][OH:20].N1C=CC=CC=1>C(O)C>[C:2]1([CH2:1][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH:17]([OH:18])[CH2:19][OH:20])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11164GlycidolHCID 804592-Benzyloxyphenol

Product 1

HCID 30220521,2-Propanediol, 3-((o-benzyloxy)phenoxy)-Yield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 49.6 g (0.248 mole) of 2-benzyloxyphenol, 22.2 g (0.3 mole) of glycidol, 2 ml of pyridine and 150 ml of absolute ethanol was heated at reflux overnight. The dark solution was concentrated to give an oil which gradually crystallized. The solid was purified by column chromatography on 1.2 kg of silica gel eluted with 0-25% acetone in benzene. Appropriate fractions were combined and concentrated to yield 49.5 g (73%) of the title compound as a white solid, mp 84°-85° C. (carbon tetrachloride) (lit.1 mp 81°-82.5° C.).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe dark solution was concentrated
  3. customto give an oil which
  4. customgradually crystallized
  5. customThe solid was purified by column chromatography on 1.2 kg of silica gel
  6. washeluted with 0-25% acetone in benzene
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-332eb4b6c0cd457a8494cb05d2667222
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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