1,2-Dichloroethane → HCID 54486581, compound

HRID 256738Notes

Reaction equation

HRID 256738 reaction equation
Cl[C:2]([CH2:4]Cl)=[CH2:3].[CH:6](=[O:10])/[CH:7]=[CH:8]/[CH3:9].C(Cl)C[Cl:13]>[Zn].C(O)(=O)C>[Cl:13][C:8]([CH2:7][CH:6]([OH:10])[CH:3]=[CH:2][CH3:4])=[CH2:9]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 65652,3-DichloropropeneHCID 447466Crotonaldehyde

Product 1

HCID 54486581HCID 54486581, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

47.50 Grams of 2,3-dichloro-1-propene were added dropwise to a mixture of 20.00 g of crotonaldehyde, 40 g of ethylene dichloride, 60 g of 3% acetic acid and 18.65 g of zinc powder at 40° C., and the resultant mixture was allowed to react at the same temperature for 5 hours. After the reaction was completed, zinc-derived insolubles were filtered off, and the resultant filtrate was subjected to separation. The organic phase was washed with a 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 to give 37.15 g of 2-chloro-1,5-heptadien-4-ol; nD25 =1.471, FI-MS m/e 146(M+), 148(M+2+).

Workup

  1. customto react at the same temperature for 5 hours
  2. filtrationwere filtered off
  3. customthe resultant filtrate was subjected to separation
  4. washThe organic phase was washed with a 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

Sources & evidence

ORD record
ord-ec209060daf747f996bab7fece96fb94
Source dataset
uspto-grants-1993_11
Patent number
US05258529

Reaction notes

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