Phenethyl alcohol

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Phenethyl alcohol
Names
IUPAC name
2-Phenylethanol
Preferred IUPAC name
2-Phenylethan-1-ol
Other names
2-Phenylethanol
Benzeneethanol
Benzyl carbinol
PEA
Phenethyl alcohol
Phenyl-2-ethanol
β-Hydroxyethylbenzene
Properties
C8H10O
C6H5CH2CH2OH
Molar mass 122.16 g/mol
Appearance Colorless viscous liquid
Odor Soft, like roses
Density 1.017 g/cm3 (20 °C)
Melting point −27 °C (−17 °F; 246 K)
Boiling point 218.2 °C (424.8 °F; 491.3 K)
2.22 g/100 ml (25 °C)
Solubility Miscible with acetone, alcohols, chloroform, glycerol, propylene glycol
Slightly soluble in mineral oil
Vapor pressure 0.09 mmHg (25 °C)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 102 °C (215.6 °F; 305 K)
Related compounds
Related compounds
Benzyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phenethyl alcohol or 2-phenylethanol, is an organic compound with the formula C8H10O.

Properties

Chemical

Oxidation of phenethyl alcohol yields phenylacetic acid.

Physical

Phenethyl alcohol is a colorless liquid, immiscible with water, but miscible with many organic solvents.

Availability

Phenethyl alcohol is sold by chemical suppliers.

It occurs widely in nature, being found in a variety of essential oils.

Preparation

Phenethyl alcohol can also be prepared by the Grignard reaction between phenylmagnesium bromide and ethylene oxide:

C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH

Industrially 2-phenylethanol is prepared via the Friedel-Crafts reaction between benzene and ethylene oxide in the presence of anhydrous Aluminium chloride.

C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl

The reaction affords the aluminium alkoxide that is subsequently hydrolyzed to the desired product.

C6H5CH2CH2OAlCl2 + H2O → C6H5CH2CH2OH + AlCl2(OH)

It is also possible to produce phenethyl alcohol by the reduction of phenylacetic acid using sodium borohydride and iodine in THF.[1]

Projects

  • Make perfumes
  • Make phenylacetic acid

Handling

Safety

Phenethyl alcohol has low toxicity and it's a safe component of perfumes and aromas.

Storage

In closed bottles.

Disposal

No special disposal is required.

References

  1. Kanth JV, Periasamy M (1991). "Selective Reduction of Carboxylic Acids into Alcohols Using NaBH and I2". Journal of Organic Chemistry. 56: 5964–5965

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