Ethylene Glycol → 2-[6-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexyl]-1,3-dioxolan

HRID 1584341Notes

Reaction equation

HRID 1584341 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[O:30])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].[CH2:31](O)[CH2:32][OH:33].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]2[O:33][CH2:32][CH2:31][O:30]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 212244777-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanal

Product 1

HCID 212244922-[6-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexyl]-1,3-dioxolanYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanal (3.8 g), ethylene glycol (1 g), p-toluenesulfonic acid monohydrate and toluene (50 ml) was stirred for 4 hours under reflux. The reaction mixture was cooled, which was then washed with water and dried (MgSO4), followed by distilling off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:3), was obtained 2-[6-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]hexyl]-1,3-dioxolan (3.9 g, 94%) as an oily product.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture was cooled
  3. washwhich was then washed with water
  4. dry with materialdried (MgSO4)
  5. distillationby distilling off the solvent under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-b2d4d51454f44ff497a2795f89241a60
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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