Formaldehyde → HCID 54364762, compound

HRID 1605836Notes

Reaction equation

HRID 1605836 reaction equation
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:3]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH:11]=1)[OH:10])[CH3:4].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[CH2:24]=O>C(O)C>[O:21]1[CH2:22][CH2:23][N:18]([CH2:24][C:8]2[C:7]([OH:12])=[CH:6][C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])=[CH:11][C:9]=2[OH:10])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diol

Product 1

HCID 54364762HCID 54364762, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.36 g (0.01 mole) of 5-(3-methyl-2-octyl)resorcinol was dissolved in 40 ml of absolute ethanol and 0.73 g (0.01 mole) of morpholine was added. The solution was cooled in ice/salt bath and 0.91 g (0.018 mole) of formaldehyde solution (37.2% w/w) was added. The temperature was kept at 5°C for 2 hours. The mixture was then slowly allowed to rise to room temperature overnight. The alcohol was removed in vacuo and the residue was dissolved in ether. The ether extract was washed with water, dried and evaporated to leave a gum which was purified by chromatography on activated magnesium silicate and eluted with 5% methanol/ether mixture. Fractions showing one spot on thin layer chromatograph (10% methanol/chloroform) were combined and evaporated to leave 2.5 g (74%) of a gum. Nmr spectra was in agreement with the structure.

Workup

  1. temperatureThe solution was cooled in ice/salt bath
  2. waitto rise to room temperature overnight
  3. customThe alcohol was removed in vacuo
  4. dissolutionthe residue was dissolved in ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. customdried
  8. customevaporated
  9. customto leave a gum which
  10. customwas purified by chromatography on activated magnesium silicate
  11. washeluted with 5% methanol/ether mixture
  12. customevaporated

Sources & evidence

ORD record
ord-c0e35d0cc3a94821842581983188aded
Source dataset
uspto-grants-1976_04
Patent number
US03951970

Reaction notes

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