Hydrochloric Acid → 15-Hydroxy-12-ketopentadecanoic acid

HRID 2372541Notes

Reaction equation

HRID 2372541 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([CH:15]1[CH2:20][CH2:19][O:18]C1=O)=[O:14])#N.[OH-:21].[K+].Cl.[OH2:24]>>[OH:18][CH2:19][CH2:20][CH2:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:1]([OH:24])=[O:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 11747922alpha-(11-Cyanoundecanoyl)-gamma-butyrolactone

Product 1

HCID 988195515-Hydroxy-12-ketopentadecanoic acidYield 93.3%

Procedure

279 g (1.00 millimole) of α-(11-cyanoundecanoyl)-γ-butyrolactone, 0.68 g (10.3 millimole) of 85% potassium hydroxide and 5.66 g of water were charged and heated under reflux over 10 hours. After completion of the reaction, the system was cooled and made acidic by use of 5 ml of 4N-HCl, followed by extraction once from 70 ml of methylene chloride and two times from 20 ml of the same. After the methylene chloride solution was dried over sodium sulfate, concentration was conducted to dryness to obtain white solid. The obtained white solid was purified with use of a silicagel column by using n-hexane/ethyl acetate (1:1, volume ratio) as a developer to obtain 0.254 g (0.933 millimole, yield: 93 %) of a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux over 10 hours
  3. customAfter completion of the reaction
  4. temperaturethe system was cooled
  5. extractionfollowed by extraction once from 70 ml of methylene chloride and two times from 20 ml of the same
  6. dry with materialAfter the methylene chloride solution was dried over sodium sulfate, concentration
  7. customto obtain white solid
  8. customThe obtained white solid was purified with use of a silicagel column

Sources & evidence

ORD record
ord-347963d26d1e45259d86a3da433e0657
Source dataset
uspto-grants-1992_03
Patent number
US05099036

Reaction notes

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