Sodium Hydroxide → HCID 54156493, compound

HRID 2198514Notes

Reaction equation

HRID 2198514 reaction equation
BrBr.[OH-:3].[Na+].[CH3:5][C:6]1([CH3:22])[C@@H:8]([C:9](=[O:11])C)[C@@H:7]1[CH:12]=[C:13]([Cl:21])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1>O.O1CCOCC1>[CH3:22][C:6]1([CH3:5])[C@@H:8]([C:9]([OH:11])=[O:3])[C@@H:7]1[CH:12]=[C:13]([Cl:21])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 86738622HCID 86738622, compound

Product 1

HCID 54156493HCID 54156493, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

13.8 g of bromine were added dropwise to a solution of 11.5 g of sodium hydroxide in 60 ml of water at 5°-10° C., and a solution of 8.1 g (0.029 mol) of trans-3,3-dimethyl-2-(2-chloro-2-(4-chloro-phenyl)-vinyl)-1-acetylcyclopropane in 30 ml of dioxane was then added dropwise at 0°-5° C. The mixture was subsequently stirred for 3 hours, without cooling, pouredonto 250 ml of water and extracted twice with 50 ml of ether each time. The aqueous phase was freed from adhering ether in vacuo and then brought to pH 2 by adding aqueous hydrochloric acid. After crystallization, the product was filtered off and rinsed with water. 6.2 g (77% of theory) of trans-3,3-dimethyl-2-(2-chloro-2-(4-chlorophenyl)-vinyl)-cyclopropanecarboxylic acid were thus obtained in the form of pale yellow-colored crystals with a melting point of 103°-106° C.

Workup

  1. temperaturewithout cooling
  2. extractionextracted twice with 50 ml of ether each time
  3. additionby adding aqueous hydrochloric acid
  4. customAfter crystallization
  5. filtrationthe product was filtered off
  6. washrinsed with water

Sources & evidence

ORD record
ord-e0cdaa3d6b37426ca44a1fb9000ac798
Source dataset
uspto-grants-1982_11
Patent number
US04358409

Reaction notes

Loading…