ChemicalBook > Product Catalog > Flavors and fragrances > Synthetic fragrances > Ketones spices > Alicyclic ketones > 4-tert-Butylcyclohexanone
4-tert-Butylcyclohexanone Chemical Properties
- Melting point:47-50 °C (lit.)
- Boiling point:113-116 °C/20 mmHg (lit.)
- Density 0.893
- refractive index 1.4570 (estimate)
- Flash point:205 °F
- storage temp. Sealed in dry,Room Temperature
- form Crystalline Powder
- color White to almost white
- Water Solubility Soluble in alcohol, ethanol (0.5g/10 mL). Insoluble in water.
- BRN 507309
- CAS DataBase Reference98-53-3(CAS DataBase Reference)
- NIST Chemistry ReferenceCyclohexanone, 4-(1,1-dimethylethyl)-(98-53-3)
- EPA Substance Registry SystemCyclohexanone, 4-(1,1-dimethylethyl)- (98-53-3)
4-tert-Butylcyclohexanone Usage And Synthesis
- Chemical PropertiesWHITE TO ALMOST WHITE CRYSTALLINE POWDER
- OccurrenceHas apparently not been reported to occur in nature.
- PreparationBy hydrogenation of p-ferr-butylphenol. Care must be taken that no free p-tert-butylphenol remains, because it is a sensitizer and depigmenting agent(Opdyke, 1974).
- PreparationN-Chlorosuccinimide (NCS) (8.0 g, 0.060 mol) and toluene (200 mL) were cooled to 0 C° in a 1-L, threenecked, round-bottomed flask equipped with a mechanical stirrer, a thermometer, a dropping funnel, and an argon inlet tube. Dimethyl sulfoxide (6.0 mL, 0.10 mol) was added and the mixture was cooled to -25 C° using a tetrachloromethane/dryice bath. A solution of 4-tert-butylcyclohexanol (6.24 g, 0.04 mol; mixture of E and Z isomers) in toluene (40 mL) was added dropwise over 5 min, stirring was continued for 2 h at -25 C°, and then a solution of triethylamine (6.0 g, 0.06 mol) in toluene (10 mL) was added dropwise over 3 min. The cooling bath was removed, and, after 5 min, diethyl ether (400 mL) was added. The organic phase was washed with 1% aq. hydrochloric acid (100 mL) and then with water (2 × 100 mL), and dried over anhydrous magnesium sulfate. The solvents were evaporated under reduced pressure, and the residue was transferred to a 50-mL, round-bottomed flask and bulb-to-bulb distilled at 120 C° (25 mmHg) to yield 5.72 g (93%) of 4-tertbutylcyclohexanone 1794; mp 41–45 C°. Recrystallization from petroleum ether at -20 C° gave an 88% recovery of 1794 with mp 45–46 C°.
- Synthesis Reference(s)Chemistry Letters, 24, p. 507, 1995
Journal of the American Chemical Society, 94, p. 7586, 1972 DOI: 10.1021/ja00776a056
Tetrahedron Letters, 16, p. 3775, 1975
- Purification MethodsPurify it via the semicarbazone (crystallised from EtOH with m 203-205o), hydrolyse this with dilute HCl and steam distil it. The distillate is extracted into Et2O, dried, evaporated and the residue is recrystallised from pentane, aqueous EtOH or EtOH [Houlihan J Org Chem 27 3860 1962]. The oxime recrystallises from 1,2-dichloropropane and has m 137.5-138.5o. [Harvill et al. J Org Chem 15 58 1950, Beilstein 7 IV 82.]
4-tert-Butylcyclohexanone Preparation Products And Raw materials
- 2,2-BIS(4-OXOCYCLOHEXYL)PROPANE SALOR-INT L156884-1EA SALOR-INT L156876-1EA 4-TERT-PENTYLCYCLOHEXANONE 4-(TERT-BUTYL)-2,6-BIS[(4-METHOXYPHENYL)METHYLENE]CYCLOHEXANONE CUCURBITACIN D LABOTEST-BB LT00007831 SALOR-INT L156892-1EA tingenone 2-METHYL-4-(1,1,2-TRIMETHYL-PROPYL)-CYCLOHEXANONE SALOR-INT L156183-1EA DATISCOSIDE DIHYDROCUCURBITACIN scopadulcic acid B tert-Butyldimethylsilyl chloride 4-tert-Butylcyclohexanol Methyl 4-tert-butylbenzoate DI-TERT-BUTYL ETHER
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