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

HRID 327646

Reaction equation

HRID 327646 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-c8b2f1c968664e6e8f59e35c9755838e
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Linked notes

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