Acetic Acid → Dehydroabietylamine acetate

HRID 1276558Notes

Reaction equation

HRID 1276558 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]2[C@:10]3([CH3:21])[C@@H:15]([CH2:16][CH2:17][C:6]=2[CH:5]=1)[C@@:14]([CH2:19][NH2:20])([CH3:18])[CH2:13][CH2:12][CH2:11]3)[CH3:3].[C:22]([OH:25])(=[O:24])[CH3:23]>C1(C)C=CC=CC=1>[CH3:3][CH:2]([C:4]1[CH:9]=[CH:8][C:7]2[C@:10]3([CH3:21])[C@@H:15]([CH2:16][CH2:17][C:6]=2[CH:5]=1)[C@@:14]([CH2:19][NH2:20])([CH3:18])[CH2:13][CH2:12][CH2:11]3)[CH3:1].[CH3:23][C:22]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 62034Dehydroabietylamine

Product 1

HCID 62418Dehydroabietylamine acetateYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Step 1--Purification of Dehydroabietylamine. A solution of dehydroabietylamine (60%, 100 g, 0.21 mol) in toluene (170 mL) was treated with a second solution of glacial acetic acid (24 mL) in toluene (55 mL) at room temperature. The mixture was stored at room temperature overnight. The crystalline salt was collected by filtration, washed with cold toluene and recrystallized from boiling toluene (152 mL). The crystals were collected by filtration, washed with n-pentane and air-dried to give dehydroabietylamine acetate (47 g, 78%) as a white crystalline solid.

Workup

  1. customStep 1--Purification of Dehydroabietylamine
  2. filtrationThe crystalline salt was collected by filtration
  3. washwashed with cold toluene
  4. customrecrystallized
  5. filtrationThe crystals were collected by filtration
  6. washwashed with n-pentane
  7. customair-dried

Sources & evidence

ORD record
ord-f9e3808a64fd484e863368a55de0f817
Source dataset
uspto-grants-2000_12
Patent number
US06166082

Reaction notes

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