Formaldehyde → 3-Morpholinomethyl-5-t-octylcatechol

HRID 2107754

Reaction equation

HRID 2107754 reaction equation
[CH2:1]=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:9]([C:17]1[CH:18]=[C:19]([OH:24])[C:20](=[CH:22][CH:23]=1)[OH:21])([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10]>C(O)(C)C>[O:6]1[CH2:7][CH2:8][N:3]([CH2:1][C:22]2[CH:23]=[C:17]([C:9]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:10])[CH3:11])[CH:18]=[C:19]([OH:24])[C:20]=2[OH:21])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 708284-Tert-octylcatechol

Product 1

HCID 2231903-Morpholinomethyl-5-t-octylcatechol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Conditions

Temperature
60 °C

Procedure

To paraformaldehyde (40 g, 1.3 mole) in 100 ml isopropanol at 25° C. was added morpholine (88 ml) in 0.5 liter isopropanol. The reaction mixture was refluxed for 30 minutes to effect solution. To the solution 4-t-octylcatechol (222 g, 1.0 mole) dissolved in 0.5 liter isopropanol was added dropwise while maintaining the solution temperature at 60° C. The reaction mixture was stirred at reflux overnight. The reaction was cooled to 25° C. and the solvent was removed in vacuo to give a white solid which was triturated with 750 ml petroleum ether and collected. Overall yield from two crops was 86%, 280 g.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. additionwas added dropwise
  3. temperatureat reflux overnight
  4. temperatureThe reaction was cooled to 25° C.
  5. customthe solvent was removed in vacuo
  6. customto give a white solid which
  7. customwas triturated with 750 ml petroleum ether
  8. customcollected
  9. customOverall yield from two crops

Sources & evidence

ORD record
ord-b5677b446ca04a8f8a0b5c4043f6e37c
Source dataset
uspto-grants-1990_06
Patent number
US04935442

Linked notes

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