4-tert-Butylcyclohexanone Property

Melting point:

47-50 °C (lit.)

Boiling point:

113-116 °C/20 mmHg (lit.)

Density 

0.893

vapor pressure 

7.91-14.2Pa at 20-25℃

refractive index 

1.4570 (estimate)

Flash point:

205 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly); Almost insoluble in water, soluble in alcohol and oils.

form 

Crystalline Powder

color 

White to almost white

Odor

Powerful, dry-camphoraceous, slightly minty odor with woody Cedar-Patchouli-like undertones.

Odor Type

woody

Water Solubility 

Soluble in alcohol, ethanol (0.5g/10 mL). Insoluble in water.

BRN 

507309

InChIKey

YKFKEYKJGVSEIX-UHFFFAOYSA-N

LogP

2.91

CAS DataBase Reference

98-53-3(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexanone, 4-(1,1-dimethylethyl)-(98-53-3)

EPA Substance Registry System

Cyclohexanone, 4-(1,1-dimethylethyl)- (98-53-3)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

GW1140000

TSCA 

Yes

HS Code 

29142990

Toxicity

Both the acute oral LD₅₀ value in rats and the acute dermal LD₅₀ value in rabbits were reported to be 5 g/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

4-tert-Butylcyclohexanone Chemical Properties,Usage,Production

Chemical Properties

WHITE TO ALMOST WHITE CRYSTALLINE POWDER

Occurrence

Has apparently not been reported to occur in nature.

Uses

4-tert-Butylcyclohexanone is used as a perfuming agents and in cosmetic. This material, commercially available for almost two decades, has only temporarily gained some importance as a powerful, “lifting” soap perfume ingredient, or as an in-expensive additive to Patchouli notes for soap and detergent fragrances, etc. It has more power and much less tenacity than Cedarwood and Patchouli, which is only an advantage in certain types of household products, where tenacity is not always very desirable. The title ketone can also give powerful “lift” to certain types of floral fragrance and to most of the herbaceous ones, Lavender, Lavandin, Rosemary, etc.

Definition

ChEBI: Cyclohexanone, 4-(1,1-dimethylethyl)- is a cyclic ketone.

Preparation

By 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).

Preparation

N-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 Methods

Purify 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.]