Epichlorohydrin → HCID 13362535, compound

HRID 1979556Notes

Reaction equation

HRID 1979556 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:5].[Cl:21][CH2:22][CH:23]1[O:25][CH2:24]1.[OH-].[NH4+]>C1(C)C=CC=CC=1>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:6]=1[C:4]1([C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[F:1])[O:25][CH:23]([CH2:22][Cl:21])[CH2:24][O:5]1

Participants

5

Reactant 3

HCID 7835Epichlorohydrin2×HCID 14923Ammonium HydroxideHCID 13362534HCID 13362534, compound

Product 1

HCID 13362535HCID 13362535, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 47 g (0.16 mol) of the end product of Example 6 in 350 ml of dry toluene was added 21.4 ml (0.18 mol) of stannic chloride, and after 5 hrs a solution of 24 ml (0.308 mol) of 1-chloro-2,3-epoxypropane in 25 ml of toluene was added with stirring over a 30 min period. After 18 hrs an additional 12 ml (0.154 mol) of 1-chloro-2,3-epoxypropane was added over a 15 min period. After 4 hrs the reaction was cooled in an ice bath and made basic with concentrated ammonium hydroxide. The reaction was filtered through celite, and the celite was washed with toluene. The combined filtrates were washed with 200 ml of water, dried over sodium sulfate, and evaporated. The resulting oil was dissolved in 100 ml of dichloromethane and chromatographed through 500 g of alumina. The column was eluted with 4 l of dichloromethane/petrol (2/1 ) to give an oil, which was about 90-95% pure by TLC. A sample was crystallized and recrystallized from ether/petrol to give white prisms: mp 117°-122° C.

Workup

  1. temperatureAfter 4 hrs the reaction was cooled in an ice bath
  2. filtrationThe reaction was filtered through celite
  3. washthe celite was washed with toluene
  4. washThe combined filtrates were washed with 200 ml of water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. dissolutionThe resulting oil was dissolved in 100 ml of dichloromethane
  8. customchromatographed through 500 g of alumina
  9. washThe column was eluted with 4 l of dichloromethane/petrol (2/1 )
  10. customto give an oil, which
  11. customA sample was crystallized
  12. customrecrystallized from ether/petrol
  13. customto give white prisms

Sources & evidence

ORD record
ord-dde42b7d37d54804b9cea322cef99c7b
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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