tert-Octylamine → HCID 136359492, compound

HRID 2193971Notes

Reaction equation

HRID 2193971 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[C:18]([NH2:26])([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:19]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[N:26][C:18]([CH3:20])([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:19])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 61017tert-OctylamineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 136359492HCID 136359492, compoundYield 94.48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a nitrogen-charged 250 mL, 4-necked round bottom flask equipped with a TEFLON-coated magnetic stirrer, a thermometer, nitrogen gas flow, addition funnel, and a Dean-Stark apparatus equipped with a condenser and a receiver was added 9.8590 g (0.042 moles) of 3,5,-di-t-butyl-4-hydroxybenzaldehyde followed by 100 mL of toluene with vigorous stirring. The solution was not clear and the aldehyde was not soluble in toluene at room temperature. 5.8 gm of t-octylamine was added into the reaction via addition funnel. The reaction flask was slowly heated to 60° C. by heating mantle, and the temperature was controlled by a THERM-O-WATCH® Controller/Monitor. The solution became clear dark reddish brown. The reaction was monitored for 2 hours at 60° C. by Thin Layer Chromatography (TLC). Then the temperature was raised to 110° C. to remove the water by azeotrope with toluene. The azeotrope of water and toluene was collected in a receiver attached to Dean-Stark. After the calculated amount of water was removed, the reaction was cooled to room temperature. The completion of the reaction was monitored by Infra Red Spectroscopy (IR) analysis and by the amount of water collected in the Dean-Stark receiver. The IR analysis confirmed the disappearance of wave number 1682 cm−1 (aldehyde C═O) and appearance of wave number 1621 cm−1 (imine C═N). The imine was collected by evaporating toluene using a rotary evaporator under water aspiration with 94.48% yield.

Workup

  1. additionTo a nitrogen-charged 250 mL, 4-necked round bottom flask
  2. customequipped with a TEFLON-coated magnetic stirrer
  3. additiona thermometer, nitrogen gas flow, addition funnel
  4. customa Dean-Stark apparatus equipped with a condenser
  5. temperatureby heating mantle
  6. temperatureThen the temperature was raised to 110° C.
  7. customto remove the water by azeotrope with toluene
  8. customThe azeotrope of water and toluene was collected in a receiver
  9. customAfter the calculated amount of water was removed
  10. temperaturethe reaction was cooled to room temperature
  11. customcollected in the Dean-Stark receiver
  12. customThe imine was collected
  13. customby evaporating toluene using
  14. customa rotary evaporator under water aspiration with 94.48% yield

Sources & evidence

ORD record
ord-592aadc59c8f479d88eca89dc9d2a43a
Source dataset
uspto-grants-2012_12
Patent number
US08329949B2

Reaction notes

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