p-Toluenesulfonic acid → HCID 56620230, compound

HRID 746011Notes

Reaction equation

HRID 746011 reaction equation
[CH3:1][O:2][C:3]([C:13]#[N:14])=[CH:4][CH:5]1[CH:7]([C:8]([O-:10])=[O:9])[C:6]1([CH3:12])[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:13]#[N:14])=[CH:4][CH:5]1[CH:7]([C:8]([OH:10])=[O:9])[C:6]1([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86740914HCID 86740914, compound

Product 1

HCID 56620230HCID 56620230, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 g of tert-butyl (1R,trans,ΔE) 3-(2-methoxy-2-cyanoethenyl)-2,2-dimethyl-cyclopropane carboxylate were dissolved in 50 ml of toluene and after 0.5 g of p-toluene sulfonic acid were added thereto, the reaction mixture was refluxed for 45 minutes, then cooled. The mixture was evaporated to dryness under reduced pressure and water and ether were added to the residue. After stirring, the decanted organic phase was evaporated to dryness under reduced pressure to obtain 3.8 g of (1R,trans,ΔE) 3-(2-methoxy-2-cyanoethenyl)-2,2-dimethyl-cyclopropane carboxylic acid melting at 125° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 45 minutes
  2. temperaturecooled
  3. customThe mixture was evaporated to dryness under reduced pressure and water and ether
  4. additionwere added to the residue
  5. customthe decanted organic phase was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-114b87e83c5f4776b0850a5803713ba6
Source dataset
uspto-grants-1986_07
Patent number
US04602038

Reaction notes

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