Ethylene Glycol → HCID 18546107, compound

HRID 1267325Notes

Reaction equation

HRID 1267325 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]=[O:24])=[CH:17][C:15]=2[N:16]=1.[CH2:25](O)[CH2:26][OH:27]>C1C=CC=CC=1>[O:24]1[CH2:25][CH2:26][O:27][CH:23]1[CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:14]2[O:13][C:12]([CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[N:16][C:15]=2[CH:17]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 18546167HCID 18546167, compound

Product 1

HCID 18546107HCID 18546107, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-[2-(2-naphthylmethyl)benzoxazol-5-yl]propionaldehyde (2.9 g), ethylene glycol (0.685 g), P-toluenesulfonic acid monohydrate (0.175 g) and benzene (50 ml) was stirred for 3 hours under reflux. The reaction mixture was successively washed with aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate (MgSO4). The solvent was distilled off, whereby 5-[2-(1,3-dioxolan-2-yl)ethyl]-2-(2-naphthylmethyl)benzoxazole (2.95 g, 89%) was obtained. Recrystallization from dichloromethane-isopropyl ether gave colorless prisms. Melting point: 85-86° C.

Workup

  1. temperatureunder reflux
  2. washThe reaction mixture was successively washed with aqueous solution of sodium hydrogencarbonate and water
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-bea459fde28d400da5c4bd875409ddc3
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Reaction notes

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