Formaldehyde → HCID 178442629, compound

HRID 2053066Notes

Reaction equation

HRID 2053066 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[C:13]([C:15]2[C:23]3[N:22]=[N:21][NH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:12](O)=[CH:11][CH:10]=1)([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[CH2:25]=[O:26].C([NH:29][CH2:30][CH3:31])C.[CH3:32][O-:33].[Na+]>CO.C1(C)C(C)=CC=CC=1>[CH2:12]([C:13]1[CH:14]=[C:9]([C:2]([CH3:1])([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:5])[CH3:6])[CH:10]=[C:11]([C:31]2[C:30]3[N:29]=[N:21][NH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:32]=1[OH:33])[C:11]1[CH:10]=[C:9]([C:2]([CH3:8])([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:5])[CH3:6])[CH:14]=[C:13]([C:15]2[C:23]3[N:22]=[N:21][NH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:25]=1[OH:26]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 10942334Sodium MethoxideHCID 178442657HCID 178442657, compound

Product 1

HCID 178442629HCID 178442629, compoundYield 157.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent

Procedure

To a container with a stirrer, 634 g of 4-(1,1,3,3-tetramethylbutyl)-6-benzotriazolyl phenol, 52 g of paraformaldehyde, 110 g of diethylamine and 600 ml of xylene were charged, and reacted at a temperature of 95 to 100° C. for 24 hours. Then, 31 g of 28% sodium methylate solution in methanol was added and reacted at a temperature of 145 to 150° C. for 10 hours. Upon completion of the reaction, the reaction solution was washed with water, 100 ml of methyl isobutyl ketone was added to the xylene layer and crystallized. The resulting crystal was filtered to obtain 594.0 g (yield 92%) of 2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazolylphenol] as white crystal (causing no dust) with a melting point of 199 to 200° C. The resulting compound had a mass of 659 (calculated value 658.9) in mass spectrometry. In addition, powder X-ray diffraction analysis with Cu-Kα radiation indicated that the resulting crystal was a crystal material having distinct diffraction peaks at diffraction angles (2θ±0.1°) of 7.1°, 8.6°, 14.3°, 16.1°, 18.1° and 23.0° as shown in FIG. 1.

Workup

  1. customreacted at a temperature of 95 to 100° C. for 24 hours
  2. customreacted at a temperature of 145 to 150° C. for 10 hours
  3. customUpon completion of the reaction
  4. washthe reaction solution was washed with water, 100 ml of methyl isobutyl ketone
  5. additionwas added to the xylene layer
  6. customcrystallized
  7. filtrationThe resulting crystal was filtered

Sources & evidence

ORD record
ord-f3e01d3348084ee3bb2a1782c72db5fd
Source dataset
uspto-grants-2008_02
Patent number
US07326744B2

Reaction notes

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