Formaldehyde → N-(Hydroxymethyl)carbazole

HRID 2051638Notes

Reaction equation

HRID 2051638 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:14]=[O:15].[OH-].[Ca+2].[OH-]>>[CH2:14]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[OH:15]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 6854CarbazoleHCID 6093208Calcium Hydroxide

Product 1

HCID 75480N-(Hydroxymethyl)carbazole

Procedure

105 parts of carbazole, 145 parts of formalin (40% W/V formaldehyde in water) and 265 parts of IMS were thoroughly mixed and then 10 parts of calcium hydroxide added. The mixture was heated with stirring at a temperature of 56° to 58° C. for an hour and thereafter filtered to remove unreacted carbazole and the calcium hydroxide. As the IMS cooled, the product N-methylol carbazole crystallised out of solution. The white crystals were separated by filtration and dried under vacuum at 50° C. for 2 hours. The crystals were identified by proton NMR and IR spectroscopy as NMC, m.p. 127°-129° C., and contained less than 1% carbazole according to gel permeation chromatography, which was used with a U.V. detector. (λ=254 mm).

Workup

  1. temperatureThe mixture was heated
  2. filtrationfiltered
  3. customto remove unreacted carbazole
  4. temperatureAs the IMS cooled
  5. customthe product N-methylol carbazole crystallised out of solution
  6. customThe white crystals were separated by filtration
  7. customdried under vacuum at 50° C. for 2 hours

Sources & evidence

ORD record
ord-aa643c5f9ff543e88a89f708eb5eb2f1
Source dataset
uspto-grants-1980_01
Patent number
US04181688

Reaction notes

Loading…