Formaldehyde → HCID 18008624, compound

HRID 987370Notes

Reaction equation

HRID 987370 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]=[CH:5][C:4]=1[OH:18].[CH2:19]=[O:20]>[Ti].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]=[C:5]([CH:19]=[O:20])[C:4]=1[OH:18]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 18008626HCID 18008626, compound

Product 1

HCID 18008624HCID 18008624, compound

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
218 °C

Procedure

A pressure reactor was charged with 500 ml of toluene and heated to 218° C. A slurry of a mixture of 2-methoxy-4-nonylphenol (250.4 g, 1.0 mol), paraformaldehyde (94.5 g, 3.15 mol), titanium cresylate (2 ml) and 50 ml of toluene was added over 5 mins. The container of slurry was washed two times with 2×50 ml of toluene. The reaction mixture was heated (the reactor was heated with a 250° C. hot oil circulating through internal coil) and stirred for 25 mins. and discharged from the reactor. The dark brown mixture was washed with 5% H2SO4 and water. The organic solution was separated and dried over MgSO4. Removal of the solvent left dark color oil as crude product. The purification was achieved through vacuums distillation and chromatography.

Workup

  1. additionwas added over 5 mins
  2. washThe container of slurry was washed two times with 2×50 ml of toluene
  3. temperatureThe reaction mixture was heated (the reactor
  4. temperaturewas heated with a 250° C. hot oil
  5. washThe dark brown mixture was washed with 5% H2SO4 and water
  6. customThe organic solution was separated
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent
  9. waitleft dark color oil as crude product
  10. customThe purification
  11. distillationwas achieved through vacuums distillation and chromatography

Sources & evidence

ORD record
ord-c658158d357343b3bbc466a0eacb2eb3
Source dataset
uspto-grants-2003_10
Patent number
US06632410B2

Reaction notes

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