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5323-87-5 - 3-Ethoxy-2-cyclohexen-1-one, 99% - A14224 - Alfa Aesar

A14224 3-Ethoxy-2-cyclohexen-1-one, 99%

CAS Number
5323-87-5
Synonyms

Size Price ($) Quantity Availability
10g 36.46
50g 122.78
250g 399.20
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3-Ethoxy-2-cyclohexen-1-one, 99%

MDL
MFCD00001580
EINECS
226-190-7

Chemical Properties

Formula
C8H12O2
Formula Weight
140.18
Boiling Point
76-78°/1mm
Flash Point
107°(224°F)
Density
1.04
Refractive Index
1.5060
Solubility
Slightly soluble in water.

Applications

3-Ethoxy-2-cyclohexen-1-one is a useful intermediate for the preparation of 3-alkyl- or aryl-2-cyclohexen-1-ones, by addition of organometallic reagents and subsequent hydrolysis. It helps in kinetic enolate formation (LDA) and alkylation occurs at the 6-position, the Stork-Danheiser kinetic alkylation procedure, which has found extensive use in alicyclic synthesis.

Notes

Store at 4°C. Protect from heat. Store away from oxidizing agents.

Literature References

Useful intermediate for the preparation of 3-alkyl- or aryl-2-cyclohexen-1-ones, by addition of organometallic reagents and subsequent hydrolysis: J. Am. Chem. Soc., 70, 2174 (1948); 72, 1645 (1950); Helv. Chim. Acta, 36, 482 (1963). For an example of this transformation in the total synthesis of axane sesquiterpenoids, see: J. Org. Chem., 61, 473 (1996):

Under conditions of kinetic enolate formation (LDA), alkylation occurs at the 6-position: the Stork-Danheiser kinetic alkylation procedure, which has found extensive use in alicyclic synthesis: J. Org. Chem., 38, 1775 (1973); Org. Synth. Coll., 7, 208 (1990) and references therein.

Other References

Beilstein
2042049
Harmonized Tariff Code
2914.50
TSCA
No

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