Ethylene Glycol → 3-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine

HRID 325680Notes

Reaction equation

HRID 325680 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)=[O:2].[CH2:24](O)[CH2:25][OH:26]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:26]1[CH2:25][CH2:24][O:2][CH:1]1[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][NH2:10]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

Product 1

HCID 127974473-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamineYield 85%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2-[3-(3-formylphenoxy)propyl]-1H-isoindole-1,3-(2H)-dione (90 g) and p-toluenesulphonic acid, monohydrate (200 mg) in benzene (900 ml) and ethane-1,2-diol (25 g) was heated under reflux using a Dean-Stark separator for 8 h. The cooled solution was washed successively with sodium carbonate solution, water, sodium chloride solution, and evaporated in vacuo. The resulting oil was dissolved in tetrahydrofuran (1 liter) and stirred with hydrazine hydrate (50 ml) at room temperature for 24 hr. The mixture was diluted with ether and filtered. The filtrate was distilled to give the title compound as a colourless oil (55.2 g) b.p. 134°-6° (0.7 mm). TLC silica; methanol:ammonia 80:1; Rf 0.4.

Workup

  1. temperatureunder reflux
  2. customfor 8 h
  3. washThe cooled solution was washed successively with sodium carbonate solution, water, sodium chloride solution
  4. customevaporated in vacuo
  5. dissolutionThe resulting oil was dissolved in tetrahydrofuran (1 liter)
  6. additionThe mixture was diluted with ether
  7. filtrationfiltered
  8. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-def86e0895e9498a9071a9f3791cb42f
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Reaction notes

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