Methanol → 6-(12-Hydroxy-1-oxododecyl)-2,3-dimethoxy-5-methylphenol

HRID 637886Notes

Reaction equation

HRID 637886 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17])(=O)C.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH3:35])[CH:28]=[C:29]([O:33]C)[C:30]=1[O:31][CH3:32].CO>ClCCCl>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([C:28]1[C:29]([OH:33])=[C:30]([O:31][CH3:32])[C:25]([O:24][CH3:23])=[CH:26][C:27]=1[CH3:35])=[O:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) ChlorideHCID 2025461712-Acetoxydodecanoyl chloride

Product 1

HCID 128326586-(12-Hydroxy-1-oxododecyl)-2,3-dimethoxy-5-methylphenolYield 75.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 12-acetoxy-n-dodecanoyl chloride (8.5 g) in 1,2-dichloroethane (30 ml) is added aluminum chloride (8.2 g) and the mixture is stirred at room temperature for 2 hours. The mixture is cooled to 5° C. and a solution of 3,4,5-trimethoxytoluene (5.6 g) in 1,2-dichloromethane (20 ml) is added to the above mixture. The mixture is stirred at room temperature for 72 hours, and at 50° C.-60° C. for 30 minutes. Methanol (200 ml) is added to the reaction mixture and the mixture is stirred at 50° C. for 3 hours. The solvent is distilled off, and the residue is subjected to extraction with dichloromethane. The dichloromethane layer is washed with water and dried over magnesium sulfate. The solvent is distilled off to thereby leave crude crystals. The product is recrystallized from ether-hexane (1:1) to give 6-(12-hydroxy-1-oxododecyl)-2,3-dimethoxy-5-methylphenol (8.5 g) as colorless needles. Melting point 82° C.

Workup

  1. temperatureThe mixture is cooled to 5° C.
  2. stirringThe mixture is stirred at room temperature for 72 hours
  3. waitat 50° C.-60° C. for 30 minutes
  4. stirringthe mixture is stirred at 50° C. for 3 hours
  5. distillationThe solvent is distilled off
  6. extractionthe residue is subjected to extraction with dichloromethane
  7. washThe dichloromethane layer is washed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent is distilled off
  10. customto thereby leave crude crystals
  11. customThe product is recrystallized from ether-hexane (1:1)

Sources & evidence

ORD record
ord-d5f30cb55522467694f8908d7c15ada0
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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