Hydroquinone → 4-[(S)-2-methyl-1-butoxy]phenol

HRID 654416

Reaction equation

HRID 654416 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH2:10][C@@H:11]([CH3:14])[CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+].C(#N)C>ClCCl>[CH3:10][C@@H:11]([CH2:12][CH3:13])[CH2:14][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 54641671-Bromo-2-methylbutane, (+)-

Product 1

HCID 14903104-[(S)-2-methyl-1-butoxy]phenolYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture of hydroquinone (18.2 grams); (S)-(+)-1-bromo-2-methylbutane (4.55 grams); anhydrous potassium carbonate (23 grams); and acetonitrile (250 mls.) was allowed to reflux for 40 hours. Flash chromatography using dichloromethane eluant yielded 2.6 grams (48%) of white crystals exhibiting a Fisher-Johns melting point of 44°-45° C. and having the structure ##STR24## confirmed by TLC, NMR, IR and mass spectral analyses.

Workup

  1. temperatureto reflux for 40 hours

Sources & evidence

ORD record
ord-64837fe3886a4e81a4bbb9a562f4bde0
Source dataset
uspto-grants-1992_07
Patent number
US05132041

Linked notes

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