2-Methyl-3-phenyl-1-propanol → Benzenepropanol, 4-(1,1-dimethylethyl)-beta-methyl-

HRID 2360962Notes

Reaction equation

HRID 2360962 reaction equation
[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][OH:4]>C1CCCCC1.ClC(Cl)C.[Fe](Cl)Cl>[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:2]([CH3:5])([CH3:3])[CH3:1])=[CH:8][CH:7]=1)[CH2:3][OH:4]

Participants

5

Reactant 1

HCID 956402-Methyl-3-phenyl-1-propanol

Product 1

HCID 92013Benzenepropanol, 4-(1,1-dimethylethyl)-beta-methyl-Yield 84%

Reagents, catalysts & solvents 3

HCID 24458Ferrous ChlorideCatalystHCID 63651,1-DichloroethaneSolventHCID 8078CyclohexaneSolvent

Procedure

DE 29 52 719 likewise describes the iron chloride-catalyzed Friedel-Crafts alkylation of 2-methyl-3-phenylpropanol. In cyclohexane or dichloroethane as solvent, a yield of 84-86% of 2-methyl-3-(4-tert-butylphenyl)propanol was obtained. The formation of the m-isomeric compound (2-methyl-3-(3-tert-butylphenyl)propanol), was not demonstrated. A disadvantage of the described Friedel-Crafts alkylations is the small amount of the m-isomeric compound formed (m:p ratio is max. 1:5).

Sources & evidence

ORD record
ord-46c9d158b7d14f4eb5e4b74b90ffabd0
Source dataset
uspto-grants-2014_04
Patent number
US08686193B2

Reaction notes

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