Pinacolone

Pinacolone

Name	Pinacolone
Synonyms	3,3-Dimethylbutanone
Name in Chemical Abstracts	3,3-Dimethyl-2-butanon
CAS No	75-97-8
EINECS No	200-920-4
Molecular formula	C6H12O
Molecular mass	100.16
SMILES code	CC(C)(C)C(=O)C

1H-NMR

1H-NMR: Pinacolone 250 MHz, CDCl3 delta [ppm] mult. atoms assignment 1.12 s 9 H CH3 tert-butyl 2.12 s 3 H CH3-C(=O)- Pinacol pinacolone rearrangement Reaction type: pinacol rearrangement, Wagner-Meerwein rearrangement Substance classes: alcohol, ketone Techniques: simultaneous distillation / extraction (SDE), column distillation, stirring with magnetic stir bar, heating with oil bath Degree of difficulty: Easy H2SO4 ; Side reactions       13C-NMR 13C-NMR: crude product 62.5 MHz, CDCl3 delta [ppm] assignment 14.1 CH3 ethyl 24.6 C1 26.3 C4, tert-butyl-CH3 44.3 C3 214.3 C2 76.5-77.5 CDCl3 3C-NMR: Pinacolone 62.5 MHz, CDCl3 delta [ppm] assignment 14.1 CH3 ethyl 24.6 C1 26.3 C4, tert-butyl-CH3 44.3 C3 214.3 C2 76.5-77.5 CDCl3 //////////////////////////////////////////// IR: Pinacolone [ATR, T%, cm-1] [cm-1] assignment 2969, 2874 aliph. C-H valence 1705 C=O valence, ketone 1355, 1365 char. for tert-butyl Substances required Batch scale: 0.01 mol 0.1 mol Pinacol Educts Amount Risk Safety Pinacol Xi 11.8 g R 38 S 37 Reagents Amount Risk Safety Sulfuric acid 24 percent C 50 mL R 35 S 1/2-26-30-45 Solvents Amount Risk Safety tert-Butyl methyl ether F Xi 40 mL R 11-38 S 2-9-16-24 Solvents for analysis Amount Risk Safety tert-Butyl methyl ether F Xi R 11-38 S 2-9-16-24 Substances produced Batch scale: 0.01 mol 0.1 mol Pinacol Products Amount Risk Safety Pinacolone F Xn 7.3 g R 11-22 S 16-20/21 Byproducts Amount Risk Safety 2,3-Dimethylbut-3-en-2-ol R no data S no data Waste Disposal acid aqueous phase (neutralize) solvent water mixtures, halogen free distillation residues organic solvents, halogen free distilled tert-butyl methyl ether solvents for rectification sulfuric acid can be reused for this reaction about five times Equipment Batch scale: 0.01 mol 0.1 mol Pinacol round bottom flask 100 mL round bottom flask 50 mL simultaneous distillation extraction (SDE) apparatus heatable magnetic stirrer with magnetic stir bar heatable magnetic stirrer with magnetic stir bar Vigreux column distillation apparatus oil bath oil bath procedure http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/3028_en.pdf   LiteratureC. J. Collins,Quart. Rev.1960,14, 357 ////////