111823-35-9 Usage
Synthesis
Triphenylmethylphosphonium iodide (8.55 g, 21.2 mmoles)
was weighed into a dry 100 mL round bottom flask, and 40 mL of
dry tetrahydrofuran were cannulated into the reaction vessel.
Phenyllithium in cyclohexane (11.8 mL of a 1.8 M solution, 21.2
mmoles) was added dropwise using an addition funnel. A color
change from yellow to dark brown was observed. The mixture was
stirred for 3 hrs at room temperature. 2,4-Dimethyl-3-pentanone (8) (2.4 g, 21.2 mmoles) was added slowly to the reaction
mixture resulting in a color change from brown to gray. After stirring
for an additional hour, a condenser was connected to the reaction
vessel, and the mixture was heated at reflux for 24 hours.The mixture was allowed to cool to room temperature and
extracted successively with aqueuos of 5% HCI, 10% NaHCO3, and
distilled water. The organic layer was separated and dried over
anhydrous MgSO4, and the drying agent was removed by gravity
filtration. The solvent was removed by fractional distillation. Gas
61
chromatographic analysis indicated the presence of 1,-
diisopropylethylene (-70%) (9), unreacted ketone (-20%) .
The distillate was purified by column chromatography on silica gel
(60-100 mesh, 2 in height and 2 in i.d.), using hexane as the eluant.
The 1,1-diisopropylethylene was identified and characterized by 1 H and 13C-NMR spectroscopy.
Check Digit Verification of cas no
The CAS Registry Mumber 111823-35-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,1,8,2 and 3 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 111823-35:
(8*1)+(7*1)+(6*1)+(5*8)+(4*2)+(3*3)+(2*3)+(1*5)=89
89 % 10 = 9
So 111823-35-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H16/c1-6(2)8(5)7(3)4/h6-7H,5H2,1-4H3
111823-35-9Relevant articles and documents
-
Whitmore,Laughlin
, p. 4392 (1932)
-
Karabatsos
, p. 1409,1412 (1960)
Alkylenation with Geminal Dialuminoalkane Reagents: The Synthesis of Olefins from Ketones
Piotrowski, Andrzej M.,Malpass, Dennis B.,Boleslawski, Marek P.,Eisch, John J.
, p. 2829 - 2835 (2007/10/02)
Bis(dichloroalumino)methane (BDAM, 1) has been synthesized in high yield from aluminum powder and methylene chloride by a published procedure carefully modified for safety.By the screening away of aluminum metal fine particles and the gradual addition of methylene bromide promoter over the course of reaction, a safe procedure was attained.Although 1 itself was a poor methylenating agent for ketones, its dietherate complex was distinctly more reactive.By exchanging half the halogens of 1 with Me3Al, MeMgBr, or Et3Al, two very effective methylenating agents for ketones, namely CH2(AlClMe)2 (2) and CH2(AlClEt)2 (3), were obtained.As diether ates with Et2O or THF, 2 and 3 smoothly converted a broad variety of ketones (aliphatic, alicyclic, and aromatic) into their corresponding methylene derivatives, with little or no competitive alkylation or reduction.A titanium-modified reagent, Cl2AlCH2TiCl3 (4), was also effective toward ketones, but gave only low conversions of esters to vinyl ethers.Finally, as an example of a multicarbon, alkylenating agent, the reagents 5-7 ((R2Al)2CH(CH2)4CH3, 5, R = Et; 6, R = Cl; and 7, R = Cl or Et) were examined.Good to fair yields of alkylenation were obtained with aromatic ketones, but aliphatic ketones underwent alkylation, hydride reduction, and/or aldol condension.The great influence of alkyl groups and donor solvent on the reactivity of 1-3 is briefly discussed.
