p-Toluenesulfonic acid → (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid

HRID 1995158Notes

Reaction equation

HRID 1995158 reaction equation
[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[C@H:3]1[C:13]([O:15]C(C)(C)C)=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:20][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[C@H:3]1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86739004tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate

Product 1

HCID 12807755(1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acidYield 80.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.4 g of the product of Step B, 100 mg of p-toluene sulfonic acid and 14 ml of toluene was stirred at 120° C. for 21/2 hours and was then evaporated to dryness under reduced pressure. The residue was crystallized from isopropyl ether, was cooled and filtered. The product was dried to obtain 900 mg of (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid melting at 98° C.

Workup

  1. customwas then evaporated to dryness under reduced pressure
  2. customThe residue was crystallized from isopropyl ether
  3. temperaturewas cooled
  4. filtrationfiltered
  5. customThe product was dried

Sources & evidence

ORD record
ord-808f4543eb984392a27702946e3d67f3
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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