Formaldehyde → HCID 178442192, compound

HRID 2051553Notes

Reaction equation

HRID 2051553 reaction equation
[CH2:1]=O.[C:3]([C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)([CH3:6])([CH3:5])[CH3:4].[C:14]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([CH2:17][CH3:18])([CH3:16])[CH3:15]>[OH-].[Na+].O1CCOCC1>[C:3]([C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:13][C:23]2[C:24]([CH3:1])=[C:19]([C:14]([CH2:17][CH3:18])([CH3:15])[CH3:16])[CH:20]=[CH:21][C:22]=2[OH:25])[CH2:11][CH2:12]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 66434-tert-PentylphenolHCID 178445677HCID 178445677, compound

Product 1

HCID 178442192HCID 178442192, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

41 3 ml (0.55 mole) of 37% strength aqueous formaldehyde solution, 85.3 g (0.55 mole) of trans-4-tertbutylcyclohexylamine, 95 g (0.579 mole) of 4-tert-pentylphenol and 1 g of sodium hydroxide are added in succession to 300 ml of dioxane at from 20° to 35° C. The mixture is then stirred for 6 hours at 70° C. and cooled to +5° C., and the precipitate is filtered off under suction, washed with 100 ml of water and then with 50 ml of dioxane and dried. 104 g (57% of theory) of trans-2-(4'-tert-butylcyclohexylamino)-methyl-4-tert-pentylphenol are obtained as white crystals of melting point 148°-150° C. (active ingredient No. 1).

Workup

  1. temperaturecooled to +5° C.
  2. filtrationthe precipitate is filtered off under suction
  3. washwashed with 100 ml of water
  4. dry with materialwith 50 ml of dioxane and dried

Sources & evidence

ORD record
ord-a2de1a0b92da42a482f9a54ed17d3e60
Source dataset
uspto-grants-1991_05
Patent number
US05019598

Reaction notes

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