Methylhydroquinone → HCID 59263665, compound

HRID 2065539Notes

Reaction equation

HRID 2065539 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7](O)[CH:6]=[CH:5][C:3]=1[OH:4].[C:10]([O-:13])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]>CC(C)=O>[CH3:20][CH:19]([CH3:21])[CH2:18][CH2:17][O:4][C:3]1[CH:5]=[CH:6][C:7]([O:13][CH2:10][CH2:1][CH:2]([CH3:8])[CH3:3])=[CH:8][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 7253MethylhydroquinoneHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium Carbonate

Product 1

HCID 59263665HCID 59263665, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under argon condition, methylhydroquinone (10.0 g, 81 mmol) and K2CO3 (5567 g, 403 mmol) were melted with 20 mL acetone and then added with 1-bromo-3-methylbutane (26.77 g, 177 mmol). Then, the mixture was agitated at reflux temperatures for 24 hours and then the temperature of the mixture was lowered to normal temperatures. After removing the solvent therefrom, the mixture was purified by column chromatography. (silica gel, CH2Cl2/hexane 1:4, Rf: 0.5). transparent oil. 1H NMR (CDCl3): 6.77 (d, 1H), 6.75 (s, 1H), 6.70 (d, 1H), 3.95 (m, 4H), 2.23 (s, 3H), 1.86 (m, 2H), 1.69 (m, 4H), 0.99 (m, 12H); 13C {1H} NMR (CDCl3): 152.9, 151.6, 128.2, 117.8, 112.2, 111.7, 67.2, 67.0, 38.4, 38.3, 25.3, 25.2, 22.8, 22.7, 16.5. Anal. Calcd, for C17H28O2: C, 77.22; H, 10.67. Found: C, 77.05; H, 10.58.

Workup

  1. temperatureat reflux temperatures for 24 hours
  2. customAfter removing the solvent
  3. customthe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-8f7e6e488c9b4b568e2b9df84799916b
Source dataset
uspto-grants-2012_10
Patent number
US08288542B2

Reaction notes

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