Lithium Chloride → Cyclopentanone, 2-(2-methyl-2-propenyl)-

HRID 486424Notes

Reaction equation

HRID 486424 reaction equation
COC([C:5]1([CH2:11][C:12]([CH3:14])=[CH2:13])[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=O.[Li+].[Cl-]>CN(P(N(C)C)(N(C)C)=O)C>[CH3:14][C:12](=[CH2:13])[CH2:11][CH:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10]

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 19391891HCID 19391891, compound

Product 1

HCID 12222022Cyclopentanone, 2-(2-methyl-2-propenyl)-

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
73 °C

Procedure

A mixture of methyl-1-(2-methyl-2-propenyl)-2-oxo-1-cyclopentanecarboxylate (78.4 g), HMPA (hexamethylphosphoramide, 250 ml) and LiCl (34 g) is heated to 73° C. for 36 hrs. Extraction (3 times, ether/water) of the reaction product provides a brown oil which, upon fractional distillation (63° C.-75° C./5.32×102Pa), yields 2-(2-methyl-2-propenyl)-1-cyclopentanone.

Workup

  1. extractionExtraction (3 times, ether/water) of the reaction product
  2. customprovides a brown oil which
  3. distillationupon fractional distillation (63° C.-75° C./5.32×102Pa)

Sources & evidence

ORD record
ord-9c32e307e20b402b87209b0f4dc12dd7
Source dataset
uspto-grants-1994_03
Patent number
US05292719

Reaction notes

Loading…