Lithium Hydroxide → Benzoic Acid

HRID 2220732Notes

Reaction equation

HRID 2220732 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1CSC1C=CC=C2C=1N=CC=C2.[Li+].[OH-]>CO.O>[C:3]([OH:22])(=[O:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59773474HCID 59773474, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.0 eq of ester 41 and 3.0 eq. of LiOH in methanol and water was heated to 65° C. for a time sufficient for completion of the hydrolysis. The mixture was cooled to room temperature and concentrated, then diluted with H2O. The pH of the aqueous mixture was adjusted to 4.5 and extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4, filtered, and concentrated to give the intermediate benzoic acid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with H2O
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ec22f5c9214a43ce9452d43aec77d015
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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