Trimethylhydroquinone → HCID 21581684, compound

HRID 268430Notes

Reaction equation

HRID 268430 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[C:7]([OH:15])=[C:8]([CH3:14])[C:9]([CH3:13])=[C:10]([CH:12]=1)O.[C:16]([O:19][CH2:20][CH2:21][C:22]([OH:26])([CH3:25])[CH:23]=[CH2:24])(=[O:18])[CH3:17]>C(Cl)Cl.[N+](C)([O-])=O>[C:16]([O:19][CH2:20][CH2:21][C:22]1([CH3:25])[CH2:23][CH2:24][C:12]2[C:10](=[C:9]([CH3:13])[C:8]([CH3:14])=[C:7]([OH:15])[C:6]=2[CH3:5])[O:26]1)(=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 12785TrimethylhydroquinoneHCID 6451240Aluminum(III) ChlorideHCID 15687733HCID 15687733, compound

Product 1

HCID 21581684HCID 21581684, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6375NitromethaneSolvent

Procedure

To an ice-cooled mixture of 3.37 g. of aluminum chloride and 40 ml. of methylene chloride was added, dropwise, 3.37 ml. of nitromethane. The resulting solution was stirred 5 minutes, and then 5.114 g. of trimethylhydroquinone was added in one portion. The green mixture was cooled to -20° and a solution of 5.35 g. of 3-hydroxy-3-methyl-4-pentenyl acetate in 20 ml. of methylene chloride was added over 1.0 hour. The mixture was allowed to warm to room temperature, kept there for 2 hours and poured into ice-H2O. The mixture was extracted with methylene chloride and the organic solutions were washed with saturated sodium bicarbonate solution and brine and dried over sodium sulfate. Solvent removal gave crude (±)-2-(2-acetoxyethyl)-6-hydroxy-2,5,7,8-tetramethylchroman as a red oil.

Workup

  1. additionmixture of 3.37 g
  2. temperatureThe green mixture was cooled to -20°
  3. waitkept there for 2 hours
  4. extractionThe mixture was extracted with methylene chloride
  5. washthe organic solutions were washed with saturated sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. customSolvent removal

Sources & evidence

ORD record
ord-adde55ae22764b0791649f7ba297c1d2
Source dataset
uspto-grants-1976_03
Patent number
US03947473

Reaction notes

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