Trimethylhydroquinone → HCID 21581684, compound

HRID 328866Notes

Reaction equation

HRID 328866 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-a7b1820e318a4e6090a5f6c1dbee70c2
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

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