3,5-Dimethylphenol → HCID 591070, compound

HRID 1382162Notes

Reaction equation

HRID 1382162 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:10][O:11]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([OH:9])[C:3]=1[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 79483,5-DimethylphenolHCID 21004Methane, dichloromethoxy-

Product 1

HCID 591070HCID 591070, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3,5-Dimethylphenol (40.0 g; 330 mmole) was dissolved in dichloromethane (210 ml) and the solution was cooled to a temperature of 0° C. Titanium tetrachloride (105 g; 553 mmole) was added dropwise over a period of 5 minutes to the stirred solution and then the temperature of the solution was maintained at 0° C. for a period of 30 minutes while dichloromethyl methyl ether (31.6 g) was added dropwise. The solution was warmed to room temperature and stirred for a period of 30 minutes and then warmed to 35° C. and stirred for a further 15 minutes. The reaction mixture was poured onto ice (ca 300 g) and the aqueous mixture was extracted with dichloromethane. The organic phase was washed three times with water and the solvent was removed by evaporation under reduced pressure. The residue was steam distilled and the distillate was extracted with dichloromethane and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 2,4-dimethyl-6-hydroxybenzaldehyde (31.0 g; 63.0%) as a yellow solid mp <50° C. Proton magnetic resonance spectrum (CDC13 ; δ in ppm): 2.19 (3H, s); 2.42 (3H, s); 6.41-6.52 (2H, m); 10.05 (1H, s); 11.90 (1H, s).

Workup

  1. additionwas added dropwise
  2. temperatureThe solution was warmed to room temperature
  3. temperaturewarmed to 35° C.
  4. stirringstirred for a further 15 minutes
  5. additionThe reaction mixture was poured onto ice (ca 300 g)
  6. extractionthe aqueous mixture was extracted with dichloromethane
  7. washThe organic phase was washed three times with water
  8. customthe solvent was removed by evaporation under reduced pressure
  9. distillationdistilled
  10. extractionthe distillate was extracted with dichloromethane
  11. customthe organic phase was separated
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-670fb20469dd47329876c3aa22c077db
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

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