1-[1-(p-Chlorophenyl)-2,2-dimethoxyethyl]cyclopropane → 1-[1-(p-Chlorophenyl)-2-methoxyvinyl]cyclopropane

HRID 1596822Notes

Reaction equation

HRID 1596822 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:14]2[CH2:16][CH2:15]2)[CH:9](OC)[O:10][CH3:11])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:14]2[CH2:16][CH2:15]2)=[CH:9][O:10][CH3:11])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 120567791-[1-(p-Chlorophenyl)-2,2-dimethoxyethyl]cyclopropane

Product 1

HCID 539422601-[1-(p-Chlorophenyl)-2-methoxyvinyl]cyclopropaneYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Water is azeotropically removed from a solution of p-toluenesulfonic acid monohydrate in toluene (150 g) until the distillate is clear. A solution of 1-[1-(p-chlorophenyl)-2,2-dimethoxyethyl]cyclopropane (24.7 g, 0.1 mol) in toluene is then added to the dried solution at 100° C. The resultant reaction mixture is refluxed for one hour, distilled to remove about 80 g of toluene/methanol, cooled to room temperature, treated with sodium carbonate (1 g), and poured into a saturated bicarbonate solution (100 mL). The organic phase is separated, washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product (20 g, 96% yield).

Workup

  1. customWater is azeotropically removed from a solution of p-toluenesulfonic acid monohydrate in toluene (150 g) until the distillate
  2. customThe resultant reaction mixture
  3. temperatureis refluxed for one hour
  4. distillationdistilled
  5. customto remove about 80 g of toluene/methanol
  6. additiontreated with sodium carbonate (1 g)
  7. additionpoured into a saturated bicarbonate solution (100 mL)
  8. customThe organic phase is separated
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86afc276550049a3915e71a4d9463045
Source dataset
uspto-grants-2001_09
Patent number
US06291721B1

Reaction notes

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