6-Methoxy-2-Acetyl Naphthalene Chemical Properties

Melting point:

110-112 °C(lit.)

Boiling point:

212-215 °C14 mm Hg(lit.)

Density 

1.0781 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Light brown to gray Solid

InChI

InChI=1S/C14H14O2/c1-3-14(15)12-5-4-11-9-13(16-2)7-6-10(11)8-12/h4-9H,3H2,1-2H3

InChIKey

LWOTXBQKJLOAOZ-UHFFFAOYSA-N

SMILES

C(C1=CC=C2C(=C1)C=CC(OC)=C2)(=O)CC

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

6-Methoxy-2-Acetyl Naphthalene Usage And Synthesis

Chemical Properties

Light yellow crystals, melting point 101-104°C.

Synthesis Reference(s)

Synthetic Communications, 20, p. 383, 1990 DOI: 10.1080/00397919008052779

General Description

6′?Methoxy-2′?propiononaphthone is a building block useful in organic synthesis. Its density has been reported.

Synthesis

Example 10 Synthesis of 1-(6-methoxynaphthalen-2-yl)propan-1-one: 29.3 g of 5-bromo-6-methoxy-2-propionyl naphthalene was dissolved in 100 ml of anhydrous dichloromethane and 20.8 ml of homotrimethylbenzene. Under strong stirring, 20 g of anhydrous aluminum chloride was added in batches to the reaction mixture that was cooled to -5 °C while the temperature was controlled below 20 °C. The reaction mixture was continued to be stirred at room temperature for 3 hours. Subsequently, the reaction mixture was slowly poured under strong stirring into a mixture consisting of 110 g of ice and 35 ml of a 35% (w/v) aqueous hydrochloric acid solution. After stirring for 15 minutes, the organic and aqueous layers were separated and the aqueous layer was discarded. The organic layer was sequentially washed twice with 50 ml of aqueous 6N hydrochloric acid solution and then with 50 ml of water. Next, 50 ml of water was added to the organic solution and the pH was adjusted with 30% (w/v) aqueous sodium hydroxide to 12. After discarding the aqueous phase, the organic phase was dried with anhydrous sodium sulfate and subsequently evaporated to dryness under vacuum. The residue was crystallized by n-heptane to give 20.2 g of 1-(6-methoxynaphthalen-2-yl)propan-1-one in 94.3% yield.

References

[1] Patent: EP440930, 1991, A2
[2] Patent: US5107013, 1992, A

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