Lithium Hydroxide → 3-(4-Tert-butylphenyl)propanoic acid

HRID 656310Notes

Reaction equation

HRID 656310 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10728414Ethyl 3-(4-(tert-butyl)phenyl)propanoate2×

Product 1

HCID 49621733-(4-Tert-butylphenyl)propanoic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound 34-3 (60 mg) prepared according to the same procedure as described in Step 2 was dissolved in 50% aqueous tetrahydrofuran solution (10 ml) and to the solution was added lithium hydroxide (24 mg). The mixture was stirred at room temperature for 5 hours to hydrolyze the compound 34-3 and the solvent was removed therefrom. The residue was dissolved in ethyl acetate and extracted to the obtain the compound 34-4 (43 mg, 81%). The compound 34-4 was dissolved in benzene (2 ml) and to the solution was added dropwise oxalyl chloride (100 μl), followed by refluxing for 2 hours. The reaction mixture obtained by concentrating the resultant under reduced pressure and hydrochloride compound 3-4 (67 mg) prepared in Example 13 were added to dichloromethane (6 ml), and to the mixture was added triethylamine (60 μl), followed by stirring at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure and the obtained residue was purified by column-chromatography (ethyl acetate/hexane=1/1) to yield the compound 34-5 (34 mg, 38%).

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionextracted to the

Sources & evidence

ORD record
ord-fcf4bf668b474968b33ada605dd6a0a7
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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