Toluene → HCID 11745138, compound

HRID 259978Notes

Reaction equation

HRID 259978 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].O>[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, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 962WaterSolvent

Procedure

45.23 Grams of 2,3-dichloro-1-propene were added dropwise to a mixture of 20.00 g of cyclohexanone, 60 g of toluene, 60 g of water and 26.65 g of zinc powder at 35° C., and after the addition, the resultant mixture was maintained at the same temperature for 5 hours. After the reaction was completed, zinc-derived insolubles were filtered off, and the resultant filtrate was separated. The organic phase thereof was washed with a 7% sodium carbonate aqueous solution, and dried over magnesium sulfate. The desiccant was filtered off, and the resultant toluene solution was concentrated under reduced pressure to give 32.75 g of 1-(2'-chloroallyl)-1-cyclohexanol; nD20 =1.495, EI-MS m/e 156 (M-H2O+), 158 (M-H2O+2+).

Workup

  1. additionafter the addition
  2. filtrationwere filtered off
  3. customthe resultant filtrate was separated
  4. washThe organic phase thereof was washed with a 7% sodium carbonate aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationthe resultant toluene solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e198c13213b94702b8616c7d2e5b739c
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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