Hydrochloric Acid → HCID 23459800, compound

HRID 2287202Notes

Reaction equation

HRID 2287202 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[CH:13]=[C:12]([C:17]([O:19]C)=[O:18])[O:11][C:10]=2[C:9]([CH2:21][CH2:22][CH3:23])=[C:8]2[C:3]=1[C:4](=[O:24])[CH2:5][CH2:6][CH2:7]2.[I-].[Li+].Cl>[OH-].[K+].O>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[O:11][C:10]=2[C:9]([CH2:21][CH2:22][CH3:23])=[C:8]2[C:3]=1[C:4](=[O:24])[CH2:5][CH2:6][CH2:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 23459796HCID 23459796, compound

Product 1

HCID 23459800HCID 23459800, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

The product from step (b) (200 mg; 0.61 mmole) in potassium hydroxide dried pyridine (5 ml) was heated on a steam bath with anhydrous lithium iodide (1 g; 7.5 mmole) for 1 hour. The mixture was cooled and concentrated hydrochloric acid diluted with an equal volume of water was added until the resulting suspension was at pH2. The product was extracted with ethylacetate, washed with water and dried (anhydrous sodium sulphate) to yield a red solid which was recrystallised from ethanol to give the title compound as red crystals (160 mg; 80%) mp 244° (decomposition).

Workup

  1. temperatureThe mixture was cooled
  2. additionwas added until the resulting suspension
  3. extractionThe product was extracted with ethylacetate
  4. washwashed with water
  5. dry with materialdried (anhydrous sodium sulphate)
  6. customto yield a red solid which
  7. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-3b7dbbd16e3942ddbb3c7b5411bf698d
Source dataset
uspto-grants-1981_05
Patent number
US04269854

Reaction notes

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