Formaldehyde → HCID 19776189, compound

HRID 1612593Notes

Reaction equation

HRID 1612593 reaction equation
[CH:1]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([SH:11])[CH:7]=[CH:8]2)=[CH:3][CH:2]=1.[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]=1[OH:26])([CH3:15])([CH3:14])[CH3:13].C=O.[CH2:29](NCCCC)CCC>C(O)C>[C:22]([C:18]1[CH:19]=[C:20]([CH:21]=[C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:17]=1[OH:26])[CH2:29][C:5]1[C:4]2[C:9](=[CH:10][CH:1]=[CH:2][CH:3]=2)[CH:8]=[CH:7][C:6]=1[SH:11])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 70582-NaphthalenethiolHCID 8148DibutylamineHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 19776189HCID 19776189, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thio-2-naphthol (16.0 g, 0.1 mol), 2,6-di-tertbutylphenol (20.6 g, 0.1 mol), paraformaldehyde (3.0 g, 0.1 mol) and di-n-butylamine (1 ml) in ethanol (100 ml) are heated, under reflux for thirteen hours, after which time thin layer chromatography shows the reaction to be complete. A small amount of solid impurity is filtered off and the solvent removed by rotary evaporation. A yellow oil is left which solidifies below 30° C. Petroleum (40°-60°) is added and a white solid (20.9 g, 55% of theory) of m.p. 30° C. is collected.

Workup

  1. temperatureunder reflux for thirteen hours
  2. customthe reaction
  3. filtrationA small amount of solid impurity is filtered off
  4. customthe solvent removed by rotary evaporation
  5. waitA yellow oil is left which
  6. customsolidifies below 30° C
  7. additionPetroleum (40°-60°) is added
  8. customa white solid (20.9 g, 55% of theory) of m.p. 30° C. is collected

Sources & evidence

ORD record
ord-79a9dce58727458b8c914d029e8185a2
Source dataset
uspto-grants-1993_03
Patent number
US05190723

Reaction notes

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