Lithium Hydroxide → HCID 4606293, compound

HRID 1619749Notes

Reaction equation

HRID 1619749 reaction equation
C[O:2][C:3](=[O:16])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1)[CH3:5].[OH-].[Li+]>CO.O>[C:12]([C:9]1[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:3]([OH:16])=[O:2])=[CH:11][CH:10]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10704172Methyl 2-(4-t-butylphenyl)propanoate

Product 1

HCID 4606293HCID 4606293, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(4-Tert-butylphenyl)propionic acid methyl ester (946 mg, 4.29 mmol) was dissolved in MeOH (10 ml) and mixed with a solution of lithium hydroxide (154 mg, 6.44 mmol) in water (5 ml). The reaction mixture was stirred for 18 h at RT. The solvent was removed under vacuum and the aqueous residue mixed with diethyl ether (30 ml). The phases were separated. The aqueous phase was reextracted with diethyl ether (20 ml). The aqueous phase was adjusted to a pH of 3 using 1 N hydrochloric acid solution. There formed a clouding or precipitation which was extracted from the aqueous phase by the addition of EtOAc (2×20 ml). The organic phase was washed with sat. NaCl solution (20 ml), dried and concentrated. 2-(4-Tert-butylphenyl)propionic acid was obtained as a colourless solid in a yield of 83% (735 mg).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe aqueous residue mixed with diethyl ether (30 ml)
  3. customThe phases were separated
  4. customThere formed
  5. customa clouding or precipitation which
  6. extractionwas extracted from the aqueous phase by the addition of EtOAc (2×20 ml)
  7. washThe organic phase was washed with sat. NaCl solution (20 ml)
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6d47975e2f884818a49de8f846eb8032
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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