Acetic Acid → Dehydroabietylamine acetate

HRID 343452Notes

Reaction equation

HRID 343452 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

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

Sources & evidence

ORD record
ord-31465b3953a745f0a1efb8203f969997
Source dataset
uspto-grants-1999_01
Patent number
US05861428

Reaction notes

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