Valproic Acid → 3-Hydroxypropyl 2-propylpentanoate

HRID 41813

Reaction equation

HRID 41813 reaction equation
[CH2:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5]([OH:7])=[O:6])[CH2:2][CH3:3].[CH2:11](O)[CH2:12][CH2:13][OH:14]>CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH2:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5]([O:7][CH2:11][CH2:12][CH2:13][OH:14])=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 3121Valproic AcidHCID 104421,3-Propanediol

Product 1

HCID 584552953-Hydroxypropyl 2-propylpentanoateYield 99%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

2-propylpentanoic acid (10.0 g, 69.3 mmol) was mixed with propane-1-3-diol (42.1 g, 555.0 mmol) and methyl-sulfonic acid (5 drops) in toluene (200 ml) and the mixture was heated under reflux using a Dean Stark trap for 12 h. After that, toluene was removed under reduced pressure and the crude mixture was dissolved in dichloromethane (200 ml) and extracted with water (pH 5, 3×200 ml). The combined organic layers were dried over sodium sulfate and the volatiles were removed under reduced pressure giving a clear oil (14.0 g, 60.0 mmol, 99%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customfor 12 h
  4. customAfter that, toluene was removed under reduced pressure
  5. dissolutionthe crude mixture was dissolved in dichloromethane (200 ml)
  6. extractionextracted with water (pH 5, 3×200 ml)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-00a9ac1db27b40b09212abd489d8cc84
Source dataset
uspto-grants-2013_09
Patent number
US08535655B2

Linked notes

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