Epichlorohydrin → HCID 13143660, compound

HRID 1979557Notes

Reaction equation

HRID 1979557 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:19][CH2:20][CH:21]1[O:23][CH2:22]1.[OH-].[NH4+]>C(Cl)(Cl)(Cl)Cl>[Cl:19][CH2:20][CH:21]1[CH2:22][O:23][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([O:2][CH3:1])=[O:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:17]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11816Methyl o-benzoylbenzoateHCID 14923Ammonium Hydroxide

Product 1

HCID 13143660HCID 13143660, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 33 g (0.138 mol) of 2-benzoyl benzoic acid methyl ester in 200 ml of dry carbon tetrachloride was added 10.1 ml (0.13 mol) of 1-chloro-3,4-epoxypropane. The reaction was cooled in an ice bath and a solution of 1.5 ml (0.013 mol) of stannic chloride in 10 ml of carbon tetrachloride was added with stirring over a 20 min period. The reaction was allowed to stand over the weekend, and then the same quantities of 1-chloro-2,3-epoxy-propane and stannic chloride were added. After 18 hours the reaction was cooled in an ice bath, and neutralized with concentrated ammonium hydroxide. The precipitate was filtered off and washed with dichloromethane and the combined filtrates were washed with 150 ml of water, dried with sodium sulfate and evaporated. The resulting oil was dissolved in 100 ml of dichloromethane and chromatographed through 500 g of neutral alumina. Elution with 3 l of dichloromethane gave the end product as an oil which was about 95% pure by TLC. Crystallization and recrystallization of a small sample from ether/petrol gave white rods, mp 90°-91° C.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. temperatureAfter 18 hours the reaction was cooled in an ice bath
  3. filtrationThe precipitate was filtered off
  4. washwashed with dichloromethane
  5. washthe combined filtrates were washed with 150 ml of water
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. dissolutionThe resulting oil was dissolved in 100 ml of dichloromethane
  9. customchromatographed through 500 g of neutral alumina
  10. washElution with 3 l of dichloromethane

Sources & evidence

ORD record
ord-1677f31008de4e498a4bd991b90559d3
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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