Lithium Hydroxide → HCID 5367576, compound

HRID 892851Notes

Reaction equation

HRID 892851 reaction equation
C([O:3][C:4](=[O:15])/[CH:5]=[CH:6]/[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.[Li+].[OH-]>C1COCC1>[C:9]1([CH2:8][CH2:7]/[CH:6]=[CH:5]/[C:4]([OH:15])=[O:3])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 5368479HCID 5368479, compound

Product 1

HCID 5367576HCID 5367576, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the intermediate 32.1 from above in 1:1 aqueous 1N LiOH:THF (250 mL) was refluxed for 18 h. It was then cooled to room temperature and washed with ethylacetate (2×200 mL). The aqueous was acidified to pH2 by the addition of conc. HCl, and extracted with ethylacetate (3×200 mL). These last organic extracts were combined, dried with MgSO4 and concentrated to afford the intermediate trans-5-phenyl-2-pentenoic acid (32.2).

Workup

  1. washwashed with ethylacetate (2×200 mL)
  2. additionThe aqueous was acidified to pH2 by the addition of conc. HCl
  3. extractionextracted with ethylacetate (3×200 mL)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-510f6bd27d3e47ce91930545e42dd3db
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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