2,6-Dimethylphenol → HCID 22398282, compound

HRID 1070884Notes

Reaction equation

HRID 1070884 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].Cl[C:11]([CH3:19])([CH2:13][CH2:14][C:15]([CH3:18])(Cl)[CH3:16])[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O>[CH3:1][C:2]1[C:7]2[C:15]([CH3:18])([CH3:16])[CH2:14][CH2:13][C:11]([CH3:19])([CH3:12])[C:6]=2[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 113352,6-DimethylphenolHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 22398282HCID 22398282, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a one necked round bottom flask 2,6-dimethylphenol (13.88 g, 113.6 mmol), 2,5-dichloro-dimethylhexane were added followed by 460 mL of nitromethane. A clear light yellow solution was cooled in a water bath. Aluminum chloride (15.2 g, 113.9 mmol) was added in small portions into the flask. The reaction mixture changed color from pale yellow to green then brown during the addition of aluminum chloride. The reaction was stirred overnight at room temperature and quenched with water. The content was extracted with ethyl acetate and washed with sodium bicarbonate and brine. Crude product was purified by plug of silica gel 5:95 ethyl acetate:hexane to obtain 19.3 g of 1,3,5,5,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-ol. 1H NMR (300 MHz, CDCl3) δ 1.40 (s, 6H), 1.67(m, 4H), 2.16 (s, 3H), 2.36 (s, 3H), 2.56 (s, 3H), 3.90 (s, 3H), 5.03(d, 1H, J=3.59 Hz), 6.33 (s, 1H), 6.89(d, 1H, J=3.59 Hz), 7.07 (s, 1H), 7.11(d, 1H, J=3.59 Hz), 8.29 (bs, 1H).

Workup

  1. temperatureA clear light yellow solution was cooled in a water bath
  2. customquenched with water
  3. extractionThe content was extracted with ethyl acetate
  4. washwashed with sodium bicarbonate and brine
  5. customCrude product was purified by plug of silica gel 5:95 ethyl acetate

Sources & evidence

ORD record
ord-4eab6c8e512d42ed9a4e32000c70d0ba
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

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