3,5-Dimethylphenol → 2-(4-Methoxybenzyl)-3,5-dimethylphenol

HRID 1247739Notes

Reaction equation

HRID 1247739 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.O.[OH-].[Li+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[OH:9])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 79483,5-DimethylphenolHCID 699934-Methyloxybenzyl chlorideHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 120856032-(4-Methoxybenzyl)-3,5-dimethylphenol

Procedure

To 3,5-dimethylphenol (12 g) were added lithium hydroxide monohydrate (4.2 g) and 4-methoxybenzyl chloride (14 mL) at 85° C., and the mixture was stirred 1.5 hours. The reaction mixture was cooled to ambient temperature and purified by column chromatography on silica gel (eluent: dichloromethane) to give 2-(4-methoxybenzyl)-3,5-dimethylphenol (5.1 g).

Workup

  1. custompurified by column chromatography on silica gel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-33ce3e040b2943f2a5e4a9f8dc4fb4e2
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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