Isobutyraldehyde → 1-Methyl-2-(2,2-dimethyl-2-formylethyl)-3-isopropenylcyclopent-1-ene

HRID 1834164Notes

Reaction equation

HRID 1834164 reaction equation
[CH3:1][C:2]1[CH2:6][CH2:5][CH:4]([C:7]([CH3:9])=[CH2:8])[C:3]=1[CH2:10]Cl.[CH:12](=[O:16])[CH:13]([CH3:15])[CH3:14].[OH-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:6][CH2:5][CH:4]([C:7]([CH3:9])=[CH2:8])[C:3]=1[CH2:10][C:13]([CH3:15])([CH3:14])[CH:12]=[O:16]

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 142178772-(Chloromethyl)-1-methyl-3-(prop-1-en-2-yl)cyclopent-1-ene

Product 1

HCID 50142621-Methyl-2-(2,2-dimethyl-2-formylethyl)-3-isopropenylcyclopent-1-eneYield 76%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 857 g (5 moles) of 1-methyl-2-chloromethyl-3-isopropenylcyclopentene and 360 g (5 moles) of isobutyraldehyde was added in the course of 5 hours, whilst stirring, to a mixture of 480 g of 50% strength sodium hydroxide solution, 24 g of tetrabutylammonium iodide and 500 ml of toluene, at 80° C. The organic phase was then separated off and washed repeatedly with 200 ml portions of water, the toluene was stripped off and the residue was distilled in a rotary evaporator; boiling point 75°-77° C/0.3 mm Hg; nD25 : 1.4788; the structure was confirmed by the nuclear resonance spectrum; yield: 76%.

Workup

  1. additionwas added in the course of 5 hours
  2. customThe organic phase was then separated off
  3. washwashed repeatedly with 200 ml portions of water
  4. distillationthe residue was distilled in a rotary evaporator

Sources & evidence

ORD record
ord-d7319b60639041a6abb927bc89f83f0f
Source dataset
uspto-grants-1978_01
Patent number
US04069258

Reaction notes

Loading…