Trimethylhydroquinone → HCID 22238285, compound

HRID 1743190Notes

Reaction equation

HRID 1743190 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10](O)[CH2:11][CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:14][C:15]1[C:16]([OH:24])=[C:17]([CH3:23])[C:18]([CH3:22])=[C:19]([CH:21]=1)[OH:20]>ClCCCl>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:21]2[C:19](=[O:20])[C:18]([CH3:22])=[C:17]([CH3:23])[C:16](=[O:24])[C:15]=2[CH3:14])[CH2:11][CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 12785TrimethylhydroquinoneHCID 411131-[4-(Propan-2-yl)phenyl]propan-1-ol

Product 1

HCID 22238285HCID 22238285, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Boron trifluoride/ethyl ether complex (1.30 g, 9.33 mmol) was dropwise added to a suspension of 1-(4-isopropylphenyl)propan-1-ol (5.00 g, 28.0 mmol) and trimethylhydroquinone (4.30 g, 28.0 mmol) in 1,2-dichloroethane (100 mL) at 60° C. in a nitrogen atmosphere, and the mixture was stirred for 3 hours at the same temperature. After cooling, the reaction mixture was washed with an aqueous solution of iron(III) chloride and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=30/1) to obtain the title compound (5.40 g, yield 62%).

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with an aqueous solution of iron(III) chloride and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c282eec160ec4cd88e1ec5bbbe84ecdb
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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