2-Phenylethanol → HCID 178479008, compound

HRID 579421Notes

Reaction equation

HRID 579421 reaction equation
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([Mg:16][Cl:17])C=CC=CC=1.C1OC1>ClC1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][O:9][Mg:16][Cl:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 6354Ethylene OxideHCID 178478979HCID 178478979, compound

Product 1

HCID 178479008HCID 178479008, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

2-phenylethanol is also prepared by the Grignard synthesis, starting from chlorobenzene, which is converted to phenyl-magnesium chloride, which then reacts with ethylene oxide to give phenylethoxy magnesium chloride. Phenylethoxy magnesium chloride thus obtained is decomposed with sulphuric acid to give 2-PEA. The main drawbacks of this process are (i) generation of potentially dangerous and air and moister sensitive phenyl-magnesium chloride (ii) requirement of sulphuric acid for the decomposition of Grignard complex and subsequent extraction of the desired product, (iii) produces large amounts of hazardous effluent and poor quality of the 2-phenylethanol which has low acceptability in perfumery industry [E. T. Theimer in Fragrance Chemistry, Academic Press, New York, (1982) p. 271].

Sources & evidence

ORD record
ord-1c3b972230d24909a6c31fe8e1248629
Source dataset
uspto-grants-2015_05
Patent number
US09040755B2

Reaction notes

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