Diethyl Ether → HCID 12833213, compound

HRID 224752Notes

Reaction equation

HRID 224752 reaction equation
[CH3:1][C:2](=[CH2:4])C.C(N(CC)CC)C.[Cl:12][C:13]([Cl:20])=[CH:14][CH2:15][CH2:16][C:17](Cl)=O.C([O:23]CC)C>>[Cl:12][C:13]([Cl:20])=[CH:14][CH:15]1[C:2]([CH3:4])([CH3:1])[CH2:17][C:16]1=[O:23]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8255IsobutyleneHCID 8471TriethylamineHCID 54074111HCID 54074111, compound

Product 1

HCID 12833213HCID 12833213, compound

Conditions

Temperature
120 °C

Procedure

84 g (1.5 mols) of isobutylene and 10.0 g (0.099 mol) of triethylamine are heated in an autoclave to 120° C. A solution of 17.35 g (0.1 mol) of 4,4-dichlorobut-3-enecarboxylic acid chloride in 35 ml of diethyl ether is then injected in the course of 30 minutes, and the reaction mixture is stirred at 120° C. for 2 hours. After cooling, the reaction mixture is triturated with diethyl ether. Solid constituents are filtered off, and the filtrate is subsequently washed with 1 N sulphuric acid (2×30 ml) as well as with 1% sodium bicarbonate solution (3×50 ml). After drying over sodium sulphate, concentration by evaporation is performed, and the residue is distilled in a bulb tube to yield 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclobutanone as colourless oil; b.p. 100°-110° C./0.5 Torr.

Workup

  1. customis then injected in the course of 30 minutes
  2. temperatureAfter cooling
  3. customthe reaction mixture is triturated with diethyl ether
  4. filtrationSolid constituents are filtered off
  5. washthe filtrate is subsequently washed with 1 N sulphuric acid (2×30 ml) as well as with 1% sodium bicarbonate solution (3×50 ml)
  6. dry with materialAfter drying over sodium sulphate, concentration by evaporation
  7. distillationthe residue is distilled in a bulb tube

Sources & evidence

ORD record
ord-d111ab38b7604e5f91aa4461067cf603
Source dataset
uspto-grants-1980_11
Patent number
US04234517

Reaction notes

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