Potassium Hydroxide → Hexadecanedioic acid, 3-methyl-

HRID 128473Notes

Reaction equation

HRID 128473 reaction equation
[CH3:1][CH:2]([CH2:7][C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[K+].O.NN>C(O)COCCO>[CH3:1][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 23469782HCID 23469782, compound

Product 1

HCID 9543664Hexadecanedioic acid, 3-methyl-Yield 91.7%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
220 °C

Procedure

35 g (0.11 mol) of 3-methyl-5-keto-hexadecanedioic acid (obtained as described under (a) above), 30.8 g (0.55 mol) of potassium hydroxide, 150 ml of diethylene glycol and 20.6 g (0.33 mol) of 80% strength hydrazine hydrate are heated to the reflux temperature for 2 hours. Water and excess hydrazine are then distilled off and the residue is heated for one hour at 220° C. When it has cooled to 15° C., the reaction mixture is acidified with hydrochloric acid and extracted with ethyl acetate. The residue which remains after removing the ethyl acetate from the organic phase is recrystallized from petroleum ether. 30.3 g (91% of theory) of 3-methyl-hexadecanedioic acid are obtained. Melting point: 77°-78° C.

Workup

  1. distillationWater and excess hydrazine are then distilled off
  2. temperatureWhen it has cooled to 15° C.
  3. extractionextracted with ethyl acetate
  4. customafter removing the ethyl acetate from the organic phase
  5. customis recrystallized from petroleum ether

Sources & evidence

ORD record
ord-8374ae2088824c96a19730610ce7171c
Source dataset
uspto-grants-1981_03
Patent number
US04259518

Reaction notes

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