1,2-Dichloroethane → HCID 22404520, compound

HRID 259982Notes

Reaction equation

HRID 259982 reaction equation
[Cl:1][C:2](CCl)=[CH2:3].[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[CH3:7].[CH2:15](Cl)CCl>[Zn].C(O)(=O)C>[Cl:1][C:2]([CH2:7][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:8])[CH3:15])=[CH2:3]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 65652,3-DichloropropeneHCID 7410Acetophenone

Product 1

HCID 22404520HCID 22404520, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

33.26 of 2,3-dichloro-1-propene were added dropwise to a mixture of 20.00 g of acetophenone, 40 g of ethylene dichloride, 60 g of 5% acetic acid and 19.52 g of zinc powder at 50° C., and the resultant mixture was allowed to react at the same temperature for 10 hours. After the reaction was completed, zinc-derived insolubles were filtered off, and the resultant filtrate was separated. The organic phase was washed with 7% sodium carbonate aqueous solution and dried over magnesium sulfate. The desiccant was filtered off, and the ethylene dichloride was distilled off under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 22.24 g of 2-chloro-4-phenyl-1-penten-4-ol; nD25 =1.536, FI-MS m/e 178(M-H2O+), 180 (M-H2O+2+).

Workup

  1. customto react at the same temperature for 10 hours
  2. filtrationwere filtered off
  3. customthe resultant filtrate was separated
  4. washThe organic phase was washed with 7% sodium carbonate aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe ethylene dichloride was distilled off under reduced pressure
  8. customThe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb7a193871524773bfe8c26031288bb6
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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