Epichlorohydrin → 1-Chloro-2-hydroxy-3-(9-oxoxanth-4-yloxy)propane

HRID 1656640Notes

Reaction equation

HRID 1656640 reaction equation
[OH:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:17]([CH:19]1[O:21][CH2:20]1)[Cl:18]>N1CCCCC1>[Cl:18][CH2:17][CH:19]([OH:21])[CH2:20][O:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 6114284-Hydroxyxanthone

Product 1

HCID 197883251-Chloro-2-hydroxy-3-(9-oxoxanth-4-yloxy)propaneYield 38%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

A mixture of 4-hydroxy-9-oxoxanthene (1.1 g), epichlorohydrin (4 g) and piperidine (0.01 g) is heated on a boiling water-bath for 5 hours. Excess epichlorohydrin is then removed by distillation and the residue is dissolved in ethyl acetate (50 ml). The organic solution is washed with 2N NaOH (20 ml) and concentrated to dryness yielding 1-chloro-2-hydroxy-3-(9-oxoxanth-4-yloxy)propane (0.6 g) as a raw product. A solution of this product in absolute ethanol (20 ml) is then added to a solution of 2-aminotetralin (0.3 g) in ethanol (10 ml) and the mixture is refluxed for 4 hours and then evaporated to dryness. The obtained residue is taken up in hydrogen chloride saturated-isopropanol affording the desired N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy -3-oxoxanth-4-yloxypropanamine hydrochloride ((i): R=H, Ar=radical 29, wherein Z is >C=0, and the chain is attached to position 2 of the tetralin moiety)(Ex. 91). Analogously, but starting from 4-hydroxyxanthene, N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-xanth-4-yloxypropanamine hydrochloride is obtained ((i): R=H, Ar=radical 29, wherein Z is a methylene group, and the chain is attached to position 2 of the tetralin moiety) (Ex. 92).

Workup

  1. temperatureis heated on a boiling water-bath for 5 hours
  2. customExcess epichlorohydrin is then removed by distillation
  3. dissolutionthe residue is dissolved in ethyl acetate (50 ml)
  4. washThe organic solution is washed with 2N NaOH (20 ml)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-522c047fb61540aabdedcacd8478a00d
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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