4-Octylphenol → HCID 6429813, compound

HRID 224520Notes

Reaction equation

HRID 224520 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:16][O:17]C(Cl)Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([C:9]1[CH:10]=[C:11]([CH:16]=[O:17])[C:12]([OH:15])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 157304-OctylphenolHCID 21004Methane, dichloromethoxy-

Product 1

HCID 6429813HCID 6429813, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

5-octylsalicylaldehyde was prepared as follows: p-octyl phenol (20.6 g) was dissolved in dry methylene chloride (400 cm3). The solution was cooled in an ice bath, stirred and treated carefully with titanium tetrachloride (44 cm3). 1,1-Dichloromethyl methyl ether (30 cm3) was then added dropwise to the cooled stirred solution. After the addition was complete, the temperature was raised to 40° C. and stirring continued for a further 15 minutes. The mixture was then poured into crushed ice (500 g) and the organic layer extracted with ether. The ethereal solution was washed several times with water, dried over anhydrous sodium sulpate and evaporated. The oily residue was purified by fractional distillation under vacuum to give 5-octylsalicylaldehyde as a colourless liquid which solidified at 30° C.

Workup

  1. custom5-octylsalicylaldehyde was prepared
  2. temperatureThe solution was cooled in an ice bath
  3. stirringstirred solution
  4. additionAfter the addition
  5. stirringstirring
  6. additionThe mixture was then poured
  7. extractionthe organic layer extracted with ether
  8. washThe ethereal solution was washed several times with water
  9. dry with materialdried over anhydrous sodium sulpate
  10. customevaporated
  11. distillationThe oily residue was purified by fractional distillation under vacuum

Sources & evidence

ORD record
ord-8ee85aa00b384ea28867859686717029
Source dataset
uspto-grants-1980_11
Patent number
US04233035

Reaction notes

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