4-(Benzyloxy)cyclohexanone Chemical Properties

Boiling point:

118-120 °C(Press: 0.14 Torr)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Methanol

form 

Oil

color 

Light Yellow

InChI

InChI=1S/C13H16O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-5,13H,6-10H2

InChIKey

FFGVIYUANJAFJS-UHFFFAOYSA-N

SMILES

C1(=O)CCC(OCC2=CC=CC=C2)CC1

Safety Information

HS Code 

2914500090

4-(Benzyloxy)cyclohexanone Usage And Synthesis

Uses

4-(benzyloxy)cyclohexanone can be used as a pharmaceutical synthesis intermediate.

Chemical Properties

Light Yellow Oil

Synthesis Reference(s)

Synthetic Communications, 26, p. 1789, 1996 DOI: 10.1080/00397919608002619

Synthesis

Synthesis of 4-(benzyloxy)cyclohexanone (14-2) Procedure: a 60% sodium hydride dispersion in mineral oil (760 mg, 23 mmol, 1.2 eq.) was slowly added to a solution of anhydrous THF (50 mL) of 1,4-dioxaspiro[4.5]decan-8-ol (14-1) (3.0 g, 19 mmol, 1.0 eq.) at 0 °C. After 6 hours of reaction, benzyl bromide (2.5 mL, 21.3 mmol, 1.1 equiv) was added dropwise to the mixture. Subsequently, the reaction mixture was stirred at room temperature overnight. After the reaction was completed, 4N HCl solution (30 mL) was added and stirring was continued for 6 hours at room temperature. The reaction mixture was neutralized with 4N sodium hydroxide solution to pH ≈ 7 and then extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by an AnaLogix automated column chromatography system using a 0 to 30% ethyl acetate/heptane gradient elution to afford the target product 14-2 (3.0 g, 77% yield) as a light yellow oil.

References

[1] Patent: WO2012/151343, 2012, A1. Location in patent: Page/Page column 36
[2] Journal of Organic Chemistry, 1970, vol. 35, # 5, p. 1525 - 1534

4-(Benzyloxy)cyclohexanone(2987-06-6)Related Product Information

• 6-Chloronicotinic acid
• 4-(Benzoyloxy)cyclohexanone
• 4-(Benzyloxy)cyclohexanone
• (2R,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone