1-Phenyl-1-propanol → beta-Methylstyrene

HRID 13728

Reaction equation

HRID 13728 reaction equation
[C:1]1([CH:7](O)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C1(C)C=CC=CC=1>[CH3:9][CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 71471-Phenyl-1-propanolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12500beta-MethylstyreneYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Compounds of Formula 1 readily catalyse the dehydration of olefins. Standard conditions were used to conduct these reactions. For example heating cyclohexanol in the presence of compounds of Formula 1 where R and R1 are hydrogen or R is hydrogen and R1 is a C1-40 alkyl, C2-40 alkenyl, C2-40 alkynyl, aryl or C1-8 alkylaryl fragment gave the desired cyclohexene. In a similar fashion treatment of 1-phenyl-1-propanol in toluene with catalysts of Formula 1 where R and R1 are hydrogen or R is hydrogen and R1 is a C1-40 alkyl, C2-40 alkenyl, C2-40 alkynyl, aryl or C1-18 alkylaryl fragment in toluene at 75° C. gave β-methyl styrene in greater than 90% yield. An advantage of this procedure is that the catalyst can simply be filtered off and reused without any apparent reduction in activity.

Workup

  1. customat 75° C.

Sources & evidence

ORD record
ord-f45002e282a147a489f12ac45ee55914
Source dataset
uspto-grants-2010_06
Patent number
US07728159B2

Linked notes

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