3,4,5-Trimethoxytoluene → HCID 12832659, compound

HRID 637908Notes

Reaction equation

HRID 637908 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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23])(=O)C.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH3:41])[CH:34]=[C:35]([O:39]C)[C:36]=1[O:37][CH3:38]>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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([C:34]1[C:35]([OH:39])=[C:36]([O:37][CH3:38])[C:31]([O:30][CH3:29])=[CH:32][C:33]=1[CH3:41])=[O:23]

Participants

5

Reactant 3

HCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) ChlorideHCID 20254621HCID 20254621, compound

Product 1

HCID 12832659HCID 12832659, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 18-acetoxy-n-octadecanoyl chloride (11 g) in 1,2-dichloroethane (50 ml) is added aluminum chloride (7 g) and the mixture is stirred at room temperature for 2 hours. This reaction mixture is cooled to 5° C. and a solution of 3,4,5-trimethoxytoluene (6.2 g) in 1,2-dichloroethane (20 ml) is added. The mixture is stirred at room temperature for 72 hours. Then, this reaction mixture is heated to 50° C.-60° C. and stirred for 30 minutes. After cooling, ice-water is added to the reaction mixture and the product is extracted with dichloromethane. The dichloromethane layer is washed with water and the solvent is distilled off to recover an oil (12.1 g). This oil is dissolved in methanol (150 ml) followed by addition of sodium hydroxide (5.2 g). The mixture is stirred at room temperature for 2 hours, at the end of which time it is neutralized with 5N-HCl and the solvent is distilled off. The resultant crude crystals are rinsed with water and recrystallized from dichloromethane-ether (1:1). The above procedure yields 6-(18-hydroxy-1-oxooctadecyl)-2,3-dimethoxy-5-methylphenol (6.4 g) as colorless needles, m.p. 101° C.

Workup

  1. temperatureThis reaction mixture is cooled to 5° C.
  2. stirringThe mixture is stirred at room temperature for 72 hours
  3. temperatureThen, this reaction mixture is heated to 50° C.-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. distillationthe solvent is distilled off
  9. customto recover an oil (12.1 g)
  10. dissolutionThis oil is dissolved in methanol (150 ml)
  11. additionfollowed by addition of sodium hydroxide (5.2 g)
  12. stirringThe mixture is stirred at room temperature for 2 hours, at the end of which time it
  13. distillationthe solvent is distilled off
  14. washThe resultant crude crystals are rinsed with water
  15. customrecrystallized from dichloromethane-ether (1:1)

Sources & evidence

ORD record
ord-8b3c282ee82b456db43c3013185d3168
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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