Toluene → HCID 22404526, compound

HRID 259980Notes

Reaction equation

HRID 259980 reaction equation
[Cl:1][C:2](CCl)=[CH2:3].[CH3:6][C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[O:10].[C:13]1(C)C=CC=CC=1>[Zn].O>[Cl:1][C:2]([CH2:11][C:9]([CH3:13])([OH:10])[CH:8]=[C:7]([CH3:12])[CH3:6])=[CH2:3]

Participants

6

Reactant 3

HCID 1140TolueneHCID 65652,3-DichloropropeneHCID 8858Mesityl oxide

Product 1

HCID 22404526HCID 22404526, 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 methyl 2-methyl-1-propenyl ketone, 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 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 toluene was distilled off under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 31.11 g of 2-chloro-4,6-dimethyl-1,5-heptadien-4-ol; nD25 =1.474, FI-MS m/e 174(M), 176(M+2).

Workup

  1. additionafter the addition
  2. filtrationwere filtered off
  3. customthe 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 toluene was distilled off under reduced pressure
  8. customThe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b5a310ced004d3089b1e1d9f17c5f65
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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