Potassium Hydroxide → HCID 10799272, compound

HRID 273943Notes

Reaction equation

HRID 273943 reaction equation
[OH-].[K+].[OH:3][CH:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:5]#[C:6][C:7]([O:9]CC)=[O:8]>C(O)C>[OH:3][CH:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:5]#[C:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19433168HCID 19433168, compound

Product 1

HCID 10799272HCID 10799272, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of potassium hydroxide (885 mg, 15.8 mmol) in 95% ethanol (35 ml) was added to ethyl 4-hydroxytridec-2-ynoate (2.68 g, 10.5 mmol) in the same solvent (5 ml) at 0°. After stirring at room temperature for 9 hours, most of the solvent was removed and water (20 ml) was added. The mixture was extracted thoroughly with dichloromethane (discarded), acidified to pH 1 with dilute hydrochloric acid and extracted with ethyl acetate. Evaporation of the dried (magnesium sulphate) ethyl acetate extracts gave an off-white solid, which on recrystallization from petroleum ether (at -78°) gave the title acid as colorless prisms: mp 65°-6°.

Workup

  1. customwas removed
  2. additionwater (20 ml) was added
  3. extractionThe mixture was extracted thoroughly with dichloromethane (discarded)
  4. extractionextracted with ethyl acetate
  5. customEvaporation of the
  6. dry with materialdried (magnesium sulphate) ethyl acetate extracts
  7. customgave an off-white solid, which
  8. customon recrystallization from petroleum ether (at -78°)
  9. customgave the title acid as colorless prisms

Sources & evidence

ORD record
ord-9eae141266f649c28fcb735203887864
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Reaction notes

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