Toluene → HCID 11745138, compound

HRID 256744Notes

Reaction equation

HRID 256744 reaction equation
[Cl:1][C:2]([CH2:4]Cl)=[CH2:3].[C:6]1(=[O:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC=CC=1>[Zn].C(O)(=O)C>[Cl:1][C:2](=[CH2:3])[CH2:4][C:6]1([OH:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 65652,3-DichloropropeneHCID 7967Cyclohexanone

Product 1

HCID 11745138HCID 11745138, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

56.53 Grams of 2,3-dichloro-1-propene were added dropwise to a mixture of 25.00 g of cyclohexanone, 75 g of toluene, 100 g of 5% acetic acid and 34.35 g of zinc powder at 45° C., and then the mixture was allowed to react at the same temperature for 3 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 sodium sulfate. The desiccant was filtered off, and then the toluene was distilled off under reduced pressure to give 44.05 g of 1-(2'-chloroallyl)-1-cyclohexanol. The results were as follows.

Workup

  1. customto react at the same temperature for 3 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 sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-865704b281e54e37a6856e16c5f5b572
Source dataset
uspto-grants-1993_11
Patent number
US05258529

Reaction notes

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