75-97-8

Basic information

• Product Name: 3,3-Dimethyl-2-butanone
• Synonyms: 3,3-Dimethyl-2-butanone;Pinakolin [German];2-Butanone,3,3-dimethyl-;3,3-Dimethylbutanone;t-butyl methyl ketone;Pinacoline;Methyl t-butyl ketone;3,3-dimethylbutan-2-one;tert-Butyl methyl ketone;2, 2-Dimethyl-3-butanone;Ketone, tert-butyl methyl;2,2-Dimethyl-3-butanone;Methyltert-butyl ketone;2-Butanone, 3,3-dimethyl-;4-01-00-03310 (Beilstein Handbook Reference);1,1,1-Trimethylacetone;2,2-Dimethylbutanone;3, 3-Dimethyl-2-butanone;Ketone, t-butyl methyl;Pinacolin;Pinakolin;Methyl tert-butyl ketone
• CAS NO: 75-97-8
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.15888
• EINECS: 200-920-4
• Mol File: 75-97-8.mol
• Article Data: 194

Chemical Properties

• Melting Point: -52.5℃
• Boiling Point: 104.9 °C at 760 mmHg
• Flash Point: 23.9 °C
• Appearance: colourless liquid
• Density: 0.802 g/cm³
• Vapor Pressure: 23.4mmHg at 25°C
• Refractive Index: 1.395
• Water Solubility: 2.44 g/100 mL (15℃)
• CAS DataBase Reference: 3,3-Dimethyl-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Dimethyl-2-butanone(75-97-8)
• EPA Substance Registry System: 3,3-Dimethyl-2-butanone(75-97-8)

Safety Data

• Hazard Codes: F:Flammable;;
• Statements: R11:; R22:
• Safety Statements: S16:; S20/21:
• Hazardous Substances Data: 75-97-8(Hazardous Substances Data)

Usage

General Description

3,3-Dimethyl-2-butanone, also known as diisobutyl ketone, is a colorless liquid organic compound with a sweet, acetone-like odor. It is a ketone with the chemical formula C6H12O and is used as a solvent in various industries such as coatings, adhesives, and printing inks. It is also used as a fragrance and flavor additive in the production of perfumes and food products. This chemical is flammable and can be hazardous if inhaled, ingested, or absorbed through the skin, so safety precautions should be taken when handling it.

InChI:InChI=1/C6H12O/c1-4-6(2,3)5-7/h5H,4H2,1-3H3

Synthetic route

2,3-dimethyl-2,3-butane diol (76-09-5) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With aluminium phosphate aluminium oxide catalyst Heating;	100%
With silica-supported orthophosphoric acid In neat (no solvent) at 180℃; for 0.5h; Catalytic behavior; Temperature; Time; Pinacol Rearrangement; Green chemistry;	100%
With [Fe3O(OOCC6H5)6(H2O)3]4[α-SiW12O40] In toluene at 99.84℃; for 6h;	80%

C6H12OS (133619-37-1) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
Ambient temperature;	100%
Ambient temperature; Yield given;

2,3-dimethyl-2,3-epoxybutane (5076-20-0) → 3,3-dimethyl-butan-2-one (75-97-8) + 2,3-dimethyl-2,3-butane diol (76-09-5) + 2,3-dimethyl-1-buten-3-ol (10473-13-9)

Conditions	Yield
With perchloric acid; sodium perchlorate at 25℃; Yields of byproduct given;	A n/a B 99.93% C n/a
With perchloric acid; sodium perchlorate at 25℃; Product distribution; heterogeneous reaction;

3,3-dimethyl-2-butanol (464-07-3, 20281-91-8) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 20℃; for 1h;	98%
With dihydrogen peroxide In water; tert-butyl alcohol at 80℃; for 24h;	97%
With Ni(NTf2)2·xH2O; 4-mercapto-4-oxide-dinaphtho<2,1-d:1',2'-f><1,3,2>dioxaphosphepin; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane at 27 - 29℃; for 20h; Inert atmosphere; Irradiation;	91%

(S)-3,3-dimethylbutan-2-ol (1517-67-5) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); acetone at 20℃; for 0.75h;	98%

pinacolone oxime (10341-64-7, 20259-50-1, 2475-93-6) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With silica gel; copper(II) nitrate In tetrachloromethane for 1h; Heating;	97%
With dihydrogen peroxide; tripropylammonium fluorochromate (VI) In acetone at 0 - 10℃; for 1.5h;	97%
With sodium tungstate; dihydrogen peroxide In water; acetone at -5 - 20℃; for 5h;	70%

3,3-dimethyl-butan-2-one-phenylhydrazone (39263-43-9) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With baker's yeast; phosphate buffer In ethanol at 37℃; for 14h;	93%
With iron(II) sulfate In chloroform at 20℃; for 1h; Hydrolysis;	91%

2-(t-butyl)-2-methyl-1,3-dithiolane (26785-73-9) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.25h; Ambient temperature;	93%

3,3,4,4-tetramethyl-1,2-dioxetane (35856-82-7) + diphenyl(methyl)phosphine (1486-28-8) → 3,3-dimethyl-butan-2-one (75-97-8) + 2,2-dihydro-4,4,5,5-tetramethyl-2-methyl-2,2-diphenyl-1,3,2-dioxaphospholane (88635-85-2)

Conditions	Yield
In benzene-d6 at 19.5℃; Kinetics; other temperatures;	A 7% B 92%
In benzene-d6 at 19.5℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, different concentrations, isotope effects; Ea, ΔS(excit);	A 8% B 92%

formaldehyd (50-00-0) + 2-methyl-2-butylchloride (594-36-5) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With hydrogenchloride; hydroquinone In diphenylether at 75℃; for 6h; Temperature; Solvent; Concentration; Reagent/catalyst;	91.1%

3,3,4,4-tetramethyl-1,2-dioxetane (35856-82-7) + dimethyl-d6-phenylphosphine (88635-84-1) → 3,3-dimethyl-butan-2-one (75-97-8) + 2,2-dihydro-4,4,5,5-tetramethyl-2,2-d6-dimethyl-2-phenyl-1,3,2-dioxaphospholane (88635-88-5)

Conditions	Yield
In benzene-d6 at 19.5℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, Ea, ΔS(excit);	A 9% B 91%
In benzene-d6 at 19.5℃;	A 9% B 91%

p-cresol (106-44-5) + (P(CH3)3)4Ru(OC(C(CH3)3)CH) → 3,3-dimethyl-butan-2-one (75-97-8) + (P(CH3)3)4Ru(OC6H4CH3)2 (125847-62-3, 131235-33-1)

Conditions	Yield
In benzene-d6 inert gas, p-cresol added as solid; not isolated; NMR;	A >99 B 91%

3,3,4,4-tetramethyl-1,2-dioxetane (35856-82-7) + Dimethyl(phenyl)phosphine (672-66-2) → 3,3-dimethyl-butan-2-one (75-97-8) + 2,2-dihydro-4,4,5,5-tetramethyl-2,2-dimethyl-2-phenyl-1,3,2-dioxaphospholane (88635-87-4)

Conditions	Yield
In benzene-d6 at 19.5℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, Ea, ΔS(excit);	A 10% B 90%
In benzene-d6 at 19.5℃;	A 10% B 90%

methylmagnesium bromide (75-16-1) + pivaloyl chloride (3282-30-2) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With aluminium trichloride; copper(l) chloride; lithium chloride In tetrahydrofuran at 10℃; for 0.166667h;	87%

2,3-dimethyl-2,3-butane diol (76-09-5) → 3,3-dimethyl-butan-2-one (75-97-8) + 2,3-dimethyl-buta-1,3-diene (513-81-5)

Conditions	Yield
With H6S2V2W16O62 at 149.84℃; for 0.5h; Reagent/catalyst; Pinacol Rearrangement;	A 82% B 16%
With SBA-15 supported zirconium In toluene at 110℃; for 2h; Pinacol rearrangement;	A 81% B 19%
With Cu2+-montmorillonit In solid at 100℃; for 1h; Product distribution; effects of homoionic-montmorillonits contains various metal ions;	A 78% B 3%

3,4,4-trimethyl-1-penten-3-ol (3732-61-4) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With lead(IV) acetate; oxygen; ozone In dichloromethane at 0℃; for 1.5h;	82%

trans-t-BuOIr(CO)(PPh3)2 (98720-65-1) + triphenylphosphine-d15 (24762-44-5) → 3,3-dimethyl-butan-2-one (75-97-8) + (P(C6H5)3)2P(C6(2)H5)3(CO)IrH

Conditions	Yield
In (2)H8-toluene Kinetics; toluene-d7, PPh3, 95°C; not sepd., detected by (1)H-NMR and mass-spectra;	A 81% B n/a

(P(CH3)3)4Ru(OC(C(CH3)3)CH) → 3,3-dimethyl-butan-2-one (75-97-8) + dihydridotetrakis(trimethylphosphino)ruthenium(II) (134002-31-6, 76171-49-8)

Conditions	Yield
With H2 In benzene-d6 inert gas, soln. of Ru-compound degassed, immersed in liquid nitrogen, exposed to H2 (450 Torr), sealed, heated to 45°C for 8 h; not isolated; NMR;	A 61% B 77%

2,3-dimethyl-2,3-epoxybutane (5076-20-0) → 3,3-dimethyl-butan-2-one (75-97-8)

Conditions	Yield
With bismuth oxide perchlorate In dichloromethane at 20℃; for 1h; Rearrangement;	75%
at 600℃;	13%
With tetrabutylammonium perchlorate In dichloromethane electrolysis; Yield given;

pinacolone oxime (10341-64-7, 20259-50-1, 2475-93-6) + acetylene (74-86-2) → 3,3-dimethyl-butan-2-one (75-97-8) + 2-tert-butyl-1H-pyrrole (5398-58-3) + O-Vinylpinacolonoxime (255376-82-0)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide; pentane at 70℃; under 12160 Torr; for 0.1h; Addition; Cyclisation; Rearrangement;	A 1.9% B 1.9% C 74.8%

tert-butylmagnesium bromide (2259-30-5) + 3-methylthio-3-N-piperidino-1-phenyl-2-propen-1-one (185245-65-2) → 3,3-dimethyl-butan-2-one (75-97-8) + 2,2-dimethylpropiophenone (938-16-9)

Conditions	Yield
In tetrahydrofuran; diethyl ether for 4h; Ambient temperature;	A n/a B 66%

3,3-dimethyl-butan-2-one (75-97-8) → 3,3-dimethyl-2-butanol (464-07-3, 20281-91-8)

Conditions	Yield
With potassium tert-butylate; hydrogen; [RuCl2(Ph2PCH2CH2NH2)2] at 20℃; under 2280 Torr; for 12h;	100%
With hydrogen; Ru((R,R)-cyP2N2)HCl In benzene-d6 at 20℃; under 2280.15 Torr; for 12h; Product distribution / selectivity; Alkaline conditions; Cooling with liquid nitrogen;	100%
With hydrogen; Ru((R,R)-cyP2(NH)2)HCl In benzene-d6 at 20℃; under 2280.15 Torr; for 12h; Product distribution / selectivity; Alkaline conditions; Cooling with liquid nitrogen;	100%

3,3-dimethyl-butan-2-one (75-97-8) → (S)-3,3-dimethylbutan-2-ol (1517-67-5)

Conditions	Yield
With potassium tert-butylate; hydrogen; [dichloro((S)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl)(α-picolylamino)ruthenium(II)] In ethanol at 25℃; under 3800.26 - 15201 Torr; for 5 - 24h; Product distribution / selectivity;	100%
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); isopropyl alcohol In 2,2,2-trifluoroethanol at 45℃; for 3h;	99%
With [dichloro((S)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl)(α-picolylamino)ruthenium(II)]; potassium tert-butylate; hydrogen In ethanol at 25℃; under 3800 Torr; for 5h;	98%

3,3-dimethyl-butan-2-one (75-97-8) → t-butylglyoxal (4480-47-1)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane; water Heating;	100%
With selenium(IV) oxide at 50℃; for 5h; Temperature;	45.5%
With selenium(IV) oxide; water In methanol for 20h; Reflux;	21%

3,3-dimethyl-butan-2-one (75-97-8) + ethylhydrazine carboxylate (4114-31-2) → (1,2,2-trimethyl-propylidene)-carbazic acid ethyl ester (78259-24-2)

Conditions	Yield
	100%
With ethanol; acetic acid
With acetic acid In ethanol

3,3-dimethyl-butan-2-one (75-97-8) + 4-iodoanisol (529-28-2) → 1-(2-methoxyphenyl)-3,3-dimethyl-2-butanone (75508-73-5)

Conditions	Yield
With potassium tert-butylate In ammonia at -33℃; Irradiation;	100%
With potassium tert-butylate In water; dimethyl sulfoxide
With hydrogenchloride; sodium amide In water; dimethyl sulfoxide

3,3-dimethyl-butan-2-one (75-97-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (2Z)-3-chloro-4,4-dimethylpent-2-enenitrile (29586-83-2)

Conditions	Yield
Stage #1: 3,3-dimethyl-butan-2-one; N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 75℃; for 4h; Stage #2: With hydroxylamine sulfate In 1,2-dichloro-ethane at 85℃; for 1h; Further stages.;	100%
Stage #1: 3,3-dimethyl-butan-2-one; N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 0 - 75℃; for 4h; Inert atmosphere; Stage #2: With hydroxylamine hydrochloride In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere;	56%
Stage #1: 3,3-dimethyl-butan-2-one; N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 0 - 75℃; for 4h; Stage #2: With hydroxylamine hydrochloride In 1,2-dichloro-ethane at 80℃; for 2h;	56%
With hydroxylamine sulfate; trichlorophosphate 1.) 1,2-dichloroethane, 50 - 55 deg C, 2 h; 70 - 75 deg C, 2 h, 2.) 85 deg C, 1 h; Yield given. Multistep reaction;

3,3-dimethyl-butan-2-one (75-97-8) + t-butyldimethylsiyl triflate (69739-34-0) → 3,3-dimethyl-2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-1-butene (84850-50-0)

Conditions	Yield
With triethylamine In benzene for 4h; Heating;	100%
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 5h; Sealed tube; Inert atmosphere;

3,3-dimethyl-butan-2-one (75-97-8) + (meso-5,10,15,20-tetra-p-tolylporphyrinato)Hf=N-2,6-diisopropylphenyl (241475-84-3) → (meso-5,10,15,20-tetra-p-tolylporphyrinato)Hf(NH-2,6-diisopropylphenyl)[OC(tBu)(=CH2)] (273927-92-7)

Conditions	Yield
With Ph3CH In benzene-d6 under N2 atm. (TTP)Hf=NAriPr, pinacolone, and Ph3CH reacted in C6D6 at 25°C for 17 h; not isolated, identified by NMR spectroscopy;	100%

2-bromo-6-methylpyridine (5315-25-3) + 3,3-dimethyl-butan-2-one (75-97-8) → 1-(6-bromopyridin-2-yl)-2,3,3-trimethylbutan-2-ol

Conditions	Yield
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #2: 3,3-dimethyl-butan-2-one In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h;	100%

3,3-dimethyl-butan-2-one (75-97-8) + benzaldehyde (100-52-7) → (E)-benzylidenepinacolone (538-44-3, 28435-47-4, 29569-91-3)

Conditions	Yield
With sodium hydroxide; dodecyl-α,ω-bis(dodecyldimethylammonium bromide) In water at 25℃; for 1.16667h; Sonication;	99%
With barium(II) hydroxide In ethanol at 20℃;	99%
barium dihydroxide In ethanol for 1h; Heating;	96%

3,3-dimethyl-butan-2-one (75-97-8) + methyloxirane (75-56-9, 16033-71-9) → 2,2-dimethyl-6-hydroxy-3-heptanone (139367-18-3)

Conditions	Yield
With lithium hexamethyldisilazane; yttrium(III) trifluoromethanesulfonate In hexane; toluene at 0℃; for 18h;	99%
With lithium perchlorate; lithium hexamethyldisilazane 1.) THF, 0 deg C, 15 min, 2.) 25 deg C, 72 h; Yield given. Multistep reaction;

3,3-dimethyl-butan-2-one (75-97-8) + trimethylsilyl cyanide (7677-24-9) → 3,3-dimethyl-2-<(trimethylsilyl)oxy>-2-cyanobutane (219860-94-3)

Conditions	Yield
With potassium carbonate at 20℃; for 4.5h;	99%
With bis(triphenylphosphine)iminium chloride at 25℃; for 1h; Inert atmosphere; Neat (no solvent);	97%
1,4-diaza-bicyclo[2.2.2]octane at 20℃;	94%
With zinc(II) iodide In dichloromethane at 0 - 20℃;

3,3-dimethyl-butan-2-one (75-97-8) + 4-chlorobenzoyl chloride (586-75-4) → 4-(3,3-dimethyl-2-oxo-butyl)-benzamide

Conditions	Yield
Stage #1: 4-chlorobenzoyl chloride With diisopropylamine; Rink-amide resin In tetrahydrofuran at 20℃; for 18h; Stage #2: 3,3-dimethyl-butan-2-one With tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 70℃; Buchwald-Hartwig coupling; Stage #3: With trifluoroacetic acid In dichloromethane at 20℃;	99%

3,3-dimethyl-butan-2-one (75-97-8) + bis(pentamethylcyclopentadienyl)dimethyl titanium → bis(η5-pentamethylcyclopentadienyl)dimethyltitanium(IV)(OC(tert-butyl)CH2)

Conditions	Yield
With methane In toluene Heating at 80°C with a slight excess of Ti-complex in toluene in a sealed tube (or under a static Ar atmosphere) for 115 h.; (1)H NMR.;	99%
With methane In toluene Heating at 100°C with a slight excess of Ti-complex in toluene in a sealed tube (or under a static Ar atmosphere) for 21 h.; (1)H NMR.;	71%

3,3-dimethyl-butan-2-one (75-97-8) + bis(diisopropylamino)chloroborane (28049-80-1) → bis(diisopropylamino)boron enolate (959925-25-8)

Conditions	Yield
With potassium hexamethyldisilazane In tetrahydrofuran byproducts: KCl; under Ar atm. to soln. KHMDS in THF ketone in THF was added dropwise at 0°C for 30 min, soln. chlorobis(dialkylamino)borane in THF was added and stirred at room temp. for 1 h; soln. was centrifugated, ppt. was filtered, volatiles were evapd. in vacuo;	99%
With sodium hexamethyldisilazane In tetrahydrofuran byproducts: NaCl; under Ar atm. to soln. NaHMDS in THF ketone in THF was added dropwise at0°C for 30 min, soln. chlorobis(dialkylamino)borane in THF was a dded and stirred at room temp. for 1 h; soln. was centrifugated, ppt. was filtered, volatiles were evapd. in vacuo;	92%
With diisopropylamine; n-butyllithium In tetrahydrofuran; hexane byproducts: LiCl; under Ar atm. to soln. i-Pr2NH in THF n-BuLi in hexane was added at -20°C and stirred for 30 min, soln. ketone in THF was added, stirred at -20°C for 30 min, chlorobis(dialkylamino)borane in THF was added, stirred at 60°C for 24 h; soln. was centrifugated, ppt. was filtered, volatiles were evapd. in vacuo;	56%

3,3-dimethyl-butan-2-one (75-97-8) + para-methylbenzylamine (104-84-7) → 2,2-dimethyl-N-(4-methylbenzyl)propan-1-imine

Conditions	Yield
With magnesium sulphate trihydrate In dichloromethane for 2h; Reflux;	99%

3,3-dimethyl-butan-2-one (75-97-8) + 1-Bromopinacolon (5469-26-1) → 5-hydroxy-2,2,5,6,6-pentamethylheptan-3-one (3205-30-9)

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78℃; for 2.41667h; Reformatsky type reaction; Inert atmosphere;	98%
With diethyl ether; magnesium; benzene
(i) Mg, EtBr, Et2O, (ii) /BRN= 1209331/, Et2O, benzene; Multistep reaction;

3,3-dimethyl-butan-2-one (75-97-8) + benzyl alcohol (100-51-6) → 4,4-dimethyl-1-phenylpentan-3-one (5195-24-4)

Conditions	Yield
With cesium hydroxide; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one)(triphenylphosphine)(dicarbonyl)iron In toluene at 90℃; for 16h; Schlenk technique; Inert atmosphere;	98%
With potassium phosphate; aluminum oxyhydroxide; palladium In toluene at 110℃; for 3h;	94%
With bis(μ-chloro)-bis[1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C(2'),N-iridium chloride]; caesium carbonate In tert-Amyl alcohol for 12h; Reflux;	86%

3,3-dimethyl-butan-2-one (75-97-8) + N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) → 3,3-dimethyl-1-butenyl-2-triflate (27701-32-2)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	98%
Stage #1: 3,3-dimethyl-butan-2-one In tetrahydrofuran at -78℃; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃;	86%
Stage #1: 3,3-dimethyl-butan-2-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃;	86%

3,3-dimethyl-butan-2-one (75-97-8) + benzene-1,2-diol (120-80-9) → 2-tert-butyl-2-methyl-1,3-benzodioxole (105732-50-1)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1h; Microwave irradiation; Reflux;	98%
With toluene-4-sulfonic acid In toluene for 24h; Reflux;	71%

3,3-dimethyl-butan-2-one (75-97-8) + triethylsilyl chloride (994-30-9) → 1-triethylsiloxy-1-tert-butylethene (51440-17-6)

Conditions	Yield
With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; hexane at -78℃; Inert atmosphere;	98%

3,3-dimethyl-butan-2-one (75-97-8) + oxalic acid diethyl ester (95-92-1) → C9H13O4(1-)*Na(1+)

Conditions	Yield
With sodium In methanol for 12h; Claisen Condensation; Inert atmosphere; Schlenk technique; Glovebox;	98%

Upstream product

• 56-23-5 tetrachloromethane 
• 21797-56-8 3,4,4-trimethyl-pent-2-enoic acid 
• 85-44-9 phthalic anhydride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 50-00-0 formaldehyd 
• 513-35-9 2-methyl-but-2-ene 
• 563-79-1 2,3-Dimethyl-2-butene 
• 60-29-7 diethyl ether 
• 677-22-5 tert-butylmagnesium chloride 
• 127-09-3 sodium acetate 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 18314-62-0 (E)-1-chloro-3,3-dimethyl-1-butene 
• 464-07-3 3,3-dimethyl-2-butanol 
• 754-10-9 2,2-dimethylpropionamide 

Downstream Products

• 34204-47-2 1-(α-Furyl)-3-tert.-butyl-1-propen-3-on 
• 29772-40-5 2,2,3-trimethyl-3-heptanol 
• 464-07-3 3,3-dimethyl-2-butanol 
• 41070-36-4 2,2-dimethyl-5-(3-pyridyl)pentane-3,5-dione 
• 6312-01-2 2,2-dimethyl-5-(4-pyridyl)pentane-3,5-dione 
• 20930-37-4 2,2,5,6,6-Pentamethyl-heptandiol-(3,5) 
• 3205-30-9 5-hydroxy-2,2,5,6,6-pentamethylheptan-3-one 
• 5340-41-0 2,2,3-trimethyl-hexan-3-ol 
• 3205-31-0 2,2,5,6,6-pentamethyl-hept-4-en-3-one 
• 36187-02-7 2,2,3,6,6-Pentamethyl-4-heptin-3-ol 
• 75-07-0 acetaldehyde 
• 13395-36-3 ethyl trimethylacetopyruvate 
• 22767-90-4 1,1,1-Trifluoro-5,5-dimethyl-2,4-hexanedione 
• 101271-74-3 1-(4-ethyl-phenyl)-3-hydroxy-3,4,4-trimethyl-pentan-1-one 

Relevant articles and documents

The role of SET in the deprotection of (thio)ketals under photosensitization by π-acceptors

Efficient deprotection of 2-methyl-2-tert-butyl-1,3-dithiolane and of the corresponding oxathiolane to give the ketone is obtained by photosensitization by a catalytic amount of aromatic nitriles (benzenetetracarbonitrile, TCB, and antracenedicarbonitrile, DCA the latter only in the presence of biphenyl) or of heterocyclic salts (triphenylpyrylium tetrafluoborate, TPPT, and methylacridinium perchlorate, MAP), in oxygen saturated solutions. The reaction involves SET to the excited π-acceptor and interception of the substrate radical cation either by oxygen (in the case of the heterocyclics) or by the superoxide anion (in the case of the nitriles). Triplet chloranil (Chl) acts both as oxidant and as proton acceptor, and thus deprotection is accompanied by formation of a stoichiometric amount of the hydroquinone ChlH2. The corresponding dioxolane is a weaker donor: SET occurs only with photoexcited TCB and causes C-C bond fragmentation, not deprotection. The other π-acceptors photosensitize the deprotection of the dioxolane, but in this case they act as Lewis acids (Chl gives a trimer under this condition). This method is unsatisfactory with protected aldehydes. The different reactivity of the radical cations of thioketals and of ketals and the scope of this deprotection method are discussed.

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Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols

We developed the first acceptorless dehydrogenation of aliphatic secondary alcohols to ketones under visible light irradiation at room temperature by devising a ternary hybrid catalyst system comprising a photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst. The reaction proceeded through three main steps: hydrogen atom transfer from the α-C-H bond of an alcohol substrate to the thiyl radical of the photo-oxidized organocatalyst, interception of the generated carbon-centered radical with a nickel catalyst, and β-hydride elimination. The reaction proceeded in high yield under mild conditions without producing side products (except H2 gas) from various alcohols, including sterically hindered alcohols, a steroid, and a pharmaceutical derivative. This catalyst system also promoted acceptorless cross-dehydrogenative esterification from aldehydes and alcohols through hemiacetal intermediates.

Production process of dichloro pinacolone (by machine translation)

The production process is characterized in that the specific production process is as follows: S1: 2 - Chloropentane preparation. S2: pinacolone. S3: pinacolone rectification. S4: synthesis of dichloro-pinacolone. S5: treatment of by-products. In addition, by adopting formaldehyde addition in the chlorination reaction, the reaction rate 3 times or more can be inhibited, and reaction and cooling can be completed between a general reaction requirement 70 - 75 hours by adding formaldehyde, and cooling by adopting chilled water, so that the production efficiency is greatly improved 20 - 25 hours. (by machine translation)