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3,4,5-Trimethoxytoluene → 6-(11-Acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol

HRID 1903426
Notes
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Reaction equation

HRID 1903426 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH3:34])[CH:27]=[C:28]([O:32]C)[C:29]=1[O:30][CH3:31]>ClCCCl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:27]1[C:28]([OH:32])=[C:29]([O:30][CH3:31])[C:24]([O:23][CH3:22])=[CH:25][C:26]=1[CH3:34])=[O:16])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) ChlorideHCID 1311378611-Chloro-11-oxoundecyl acetate

Product 1

HCID 204311686-(11-Acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenolYield 79.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution (150 ml) of 11-acetoxy-n-undecanoyl chloride (27.6 g) in 1,2-dichloroethane is added aluminum chloride (28 g), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is cooled to 5° C. followed by addition of a solution (50 ml) of 3,4,5-trimethoxytoluene (19.1 g) in 1,2-dichloroethane and the whole mixture is stirred at room temperature for 72 hours. The reaction mixture is then heated to 50°-60° C. and stirred for 30 minutes. After cooling, 300 ml of ice water is added to the reaction mixture and the product is extracted with dichloromethane. The dichloromethane layer is washed with water and dried over anhydrous magnesium sulfate, and the solvent is distilled off to give a light-yellow oil of 6-(11-acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol (33 g).

Workup

  1. temperatureThe reaction mixture is cooled to 5° C.
  2. stirringthe whole mixture is stirred at room temperature for 72 hours
  3. temperatureThe reaction mixture is then heated to 50°-60° C.
  4. stirringstirred for 30 minutes
  5. temperatureAfter cooling
  6. extractionthe product is extracted with dichloromethane
  7. washThe dichloromethane layer is washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-8ef1e1c66ddf456eb36f569ded189789
Source dataset
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04436753

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes