Sodium Hydroxide → Dehydroabietylamine

HRID 363528Notes

Reaction equation

HRID 363528 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].CC(O)=O.[OH-].[Na+]>O>[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]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 62418Dehydroabietylamine acetate

Product 1

HCID 62034DehydroabietylamineYield 76.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of dehydroabietylamine acetate (47 g, 0.16 mol) in water (175 mL) was gently warmed until the solution became homogeneous. An aqueous solution of NaOH (10% W/V, 61 mL) was carefully added and after cooling to room temperature. The aqueous solution was extracted with diethyl ether, dried over MgSO4, filtered and concentrated to give dehydroabietylamine (35 g, 58%) as a viscous oil which solidified on standing.

Workup

  1. extractionThe aqueous solution was extracted with diethyl ether
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f7cc65ec77524b5388ddbc7f2f21b0d8
Source dataset
uspto-grants-1999_02
Patent number
US05874473

Reaction notes

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