Octanoic Acid → 2-Dimethylamino-2-methyl-1-propyl caprylate

HRID 2397876

Reaction equation

HRID 2397876 reaction equation
[CH3:1][C:2]([N:6]([CH3:8])[CH3:7])([CH2:4][OH:5])[CH3:3].[C:9](O)(=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C1(C)C=CC=CC=1>[C:9]([O:5][CH2:4][C:2]([N:6]([CH3:8])[CH3:7])([CH3:3])[CH3:1])(=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 379Octanoic AcidHCID 234352-(Dimethylamino)-2-methylpropanol

Product 1

HCID 545277552-Dimethylamino-2-methyl-1-propyl caprylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

DMAMP 118 g (1 mole) and commercial grade caprylic acid 131 g (1 mole) were dissolved in 35 ml of toluene. The mixture was heated under reflux at about 140°-165° until 20 ml distillate was recovered and no more was being collected. The pressure was then reduced to 10mm and distillation was continued to about 130° C to strip off toluene and water. The pressure was then reduced to about 1 mm and the main product fraction was recovered at a liquid temperature of about 106°-109°. There was obtained 2-dimethylamino-2-methyl-1-propyl caprylate, neutral equivalent 247.9 compared with theoretical 244.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux at about 140°-165° until 20 ml distillate
  3. customwas recovered
  4. customno more was being collected
  5. distillationThe pressure was then reduced to 10mm and distillation
  6. customwas continued to about 130° C
  7. customthe main product fraction was recovered at a liquid temperature of about 106°-109°

Sources & evidence

ORD record
ord-e4a6d84bc127406c9fda6e0c26d748d4
Source dataset
uspto-grants-1977_05
Patent number
US04022909

Linked notes

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